


My Mistake

by miss_molly



Category: Supernatural
Genre: Abusive John Winchester, Age Difference, Alcoholic John Winchester, Alternate Universe - High School, Alternate Universe - Modern Setting, Angst and Feels, Begging, Bisexual Dean Winchester, Blow Jobs, Bottom Castiel (Supernatural), Bottom Dean Winchester, Cheating, Come Swallowing, Consensual Sex, Dead Mary Winchester, Dean Has Scars from John, Dirty Talk, Drunken Flirting, Drunken Kissing, F/F, F/M, Face-Fucking, Fluff, Football Captain Dean, Forbidden Love, Foreplay, Gay Castiel (Supernatural), Hickeys, History Teacher Castiel (Supernatural), Hurt Dean Winchester, John Winchester's A+ Parenting, Lacrosse Captain Dean, Light Masochism, Light Sadism, Lingerie, M/M, Middle School Student Sam Winchester, Protective Dean Winchester, Resolved Sexual Tension, Sexual Fantasy, Sexual Tension, Slow Build Castiel/Dean Winchester, Slow Burn, Smut, Spanking, Student Dean Winchester, Student!Dean, Switching, Teacher-Student Relationship, Teasing, Top Castiel (Supernatural), Top Dean Winchester, Underage Drinking, a lot more - Freeform, dean is almost 18, teacher!Castiel
Language: English
Status: In-Progress
Published: 2020-10-15
Updated: 2021-03-08
Packaged: 2021-03-08 19:28:41
Rating: Mature
Warnings: Graphic Depictions Of Violence, Major Character Death, Underage
Chapters: 7
Words: 23,452
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27022030
Author URL: https://archiveofourown.org/users/miss_molly/pseuds/miss_molly
Summary: This started out as a drabble but I'm making it REALLY long.1. "I wish I could hate you"2. "If you really love me you'll let me go."3. "You heard me. Take. It. Off."Dean is having trouble at home and a generous Castiel lends a therapeutic hand, but what happens when one or both of them feel something more? Dean is working three jobs to help get Sam and him into a better life.Sample:Castiel’s eyebrows didn’t budge. “Take off your shirt, let me see.”“What??? No!” Dean exclaimed pulling down on his sleeves again.“Yes, you heard me. Take. It. Off.” The teacher enunciated every word.“Why? You’re not going to find anything spectacular.” He tried playing it cool one more time.
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester, a bunch of others - Relationship
Comments: 22
Kudos: 85





	1. Slip Ups

**Author's Note:**

> I hope you guys like this, I just hope someone finds it haha. This is my first work I've every posted anywhere and I'm nervous. I really like this work and I want to upload pretty regularly, maybe bi weekly or something. I hope you enjoy.

Dean stumbled out of the small bathroom stall on the third floor of Lawrence High School, honestly a little more than buzzed from the whiskey sloshing around in his water bottle. It wasn’t his proudest moment, but he made it back to class and thought he was concealing it pretty well, aside from Charlie’s nudge and whisper “I can smell the alcohol on you, it’s less than appetizing”

He just scoffed and mumbled a half hearted apology while taking his seat next to her.

“I wish I could hate you, oh my gosh, you’re so stupid.” Charlie sighed at her best friend. 

“You’re just jealous of me,” Dean slurred in a whisper.

“I am most definitely NOT jealous of you” she snapped back a little louder than she meant to. Their history teacher, Mr. Novak, overheard this, and a few other students looked along as he walked over to the wild redhead. His blue tie made his eyes pop and the slacks he was wearing shaped him perfectly and he knew it.

“Ah, and what are we not jealous of over there miss Bradbury?” He questioned, eyeing Dean as she nervously looked around the room.

Charlie let out a nervous chuckle and said “I am soooo not jealous that Dean liked boys and I don’t” she ended confidently, but earned a heavy glare from Dean.

“I like giiirlss too!” Dean exclaimed with a slur to his words which Novak picked up on, but skipped over for the time being. He walked back to the front of the classroom and continued his lesson on the Vietnam war.

When he wrapped up the lesson with around five minutes left of class he went over what they were supposed to do for homework, watch a video and answer eight questions. After everyone had acknowledged that they had homework, he let them talk amongst themselves. Castiel found himself listening extra close to a certain conversation.

“You are quite possibly the worst friend on the entire planet,” Dean said in a low voice as he turned to Charlie.

“HEY! I was just covering your drunk ass, don’t go blaming me for any of this” she replied rolling her eyes “I was just thinking on the fly, I’m sorry for saying something that everyone in class already knew”

“Yeah, all the students, dumbass, I try to keep my sexuality quiet around teachers so they don’t, ya know tell my father” Dean sighed seeming defeated. His father always brought down his mood and sobered him up quicker than he could say ‘Sammy.’ “I’m going to apologize to Mr. Novak after class and explain the situation to him, tell Mrs. Klein I’ll be a little late to culinary”

The bell rang and everyone shot out the door, “I’ll try to get a pass” Dean mumbled to Charlie as she finished packing her bag.

He stopped at Mr. Novak’s desk and waited until no one was in the classroom before he started to speak. “M-mister Novak” he stuttered, getting his attention from the chalk board.

Castiel turned around and met a slouched insecure boy, the total opposite from what he was used to seeing in class and in the hallways.

“Drinking in school is highly frowned upon, Dean. I think you know that though” he said turning back to the chalkboard.

“Right I know that, I just wanted to get through the day a little faster, I’m sorry for interrupting your class. I do, however, need to talk to you about what was said…” Dean trailed off getting more shy and tracing his thumb over the necklace his brother gave him a few years ago for Christmas.

“About you liking boys? Or girls? Or both?” His teacher queried sitting back at his desk with an annoying smirk.

“B-both, the whole concept of being bisexual really, everyone at school knows, but I strongly prefer that it does not get back home to my father, because that would not be good” he chuckled and scratched the back of his head, his shirt sleeve pulled up and revealed a circular burn mark that Castiel was immediately drawn to.

Eyes wide he asked “What happened to your arm?” Using a very concerned voice

Dean gasped and pulled his sleeve down, “Oh, I was cooking dinner for my little brother the other night and grease popped onto my arm and I -“ his sentence was cut off by the bell

Mr. Novak wrote out a pass for him, “Come see me after school, okay?” Dean could tell he his story was not going to fly with his history teacher. He nodded his head quickly and scurried out of the classroom and down the stairs to the culinary rooms. He put his pass on Mrs. Klein’s desk and found Charlie.

“How did it go?” His friend whispered immediately, ignoring their teacher explaining safety rules. 

“He wants me to stay after school, he saw something on my wrist,” Dean sighed and tugged at his sleeve

“Heyyyy, maybe it's just because he thinks you’re cute” Charlie joked, in a feeble attempt to get her friend to smile, with no such luck

“Charlie you don’t know what this means, if Novak finds out what John has done, he is legally obligated to report it to the school and that means that Sam and I would go into foster care. I just have to hold on until next year, and I can legally become Sam’s guardian. Charlie it’s just one more year I’ve been dealing with this my whole life.” Dean’s voice cracked and his eyes watered.

Charlie’s heart broke for him, “Dean, it’s okay I’m here with you always, you’ll make it one more year, I’ll even pretend to be your girlfriend” she placed her hand on his forearm and stopped him from shaking.

“Ha ha ha” he said dryly cracking a smile.

“All right everyone go to your usual stations with your groups, the recipe is on the board, let me know if you need any help!” Mrs. Klein exclaimed, bringing the whole class out of their haze. Chairs scratched the floor and his classmates made their ways to their stations. In the blink of an eye they were eating some kind of stir-fry and the bell was ringing sending Dean and Charlie to different classes.

Dean always hated science, most of the time it made him queasy, not to mention the classroom was all the way across the school and up three flights of stairs. He rushed there through students congregating with their friends in the hallway, and made it just in time for the bell. Immediately inside he saw his friend - honestly he didn’t know what they were - Benny, who laughed and pulled out a chair next to him. Throwing his bag down he sat next to Benny who laughed again and put his hand on Dean’s thigh - Dean really didn’t know what to classify Benny as, a friend? boyfriend? friends with benefits? They were definitely something.

Benny’s laugh was gruff and loud, and made Dean jump a little. Combined with the hand on his thigh Benny whispered “hey cutie” in his ear, almost growling, and god did that make Dean feel things he didn’t want to feel in school.

Mrs. MacLeod - or ‘evil ginger bitch’ as Dean preferred - started the class by scratching her long, neon acrylics on the chalkboard. Half the class moaned and the other half moaned and covered their ears. At least Benny took his hand off of Dean’s thigh.

“Well, I think that got everyone’s attention, that was scientifically one of the worst sounds to the human ear, often equated with a scream or a baby crying. Can anyone tell me the different types of sound waves?”

Dean was getting ready to raise his hand when he felt that familiar hand back on his thigh. He gasped and reached his hand down to lace with Benny’s. “Not today, please” Dean’s voice was quiet, but serious nonetheless, his eyes piercing into the other boy’s. Benny nodded and held his friend’s hand for the entirety of class, just running his thumb across Dean’s knuckles.

Science wasn’t so bad that day, but he dreaded the end of class because that meant only 45 more minutes until he had to confront Mr. Novak again. Thank whatever holy thing there was above that he had art with Charlie last period every day. The last ten minutes of Ms. MacLeod’s class were spent flirting with Benny and getting payback from the beginning of class, once Benny let out a slight moan Dean shot up and walked to the door and the bell rang. He bolted down the stairs before they got too crowded and made the way to Ms. Master’s art classroom.

Charlie beat him there and saved him a seat. Class went by too quickly and all Dean managed was a few shaky scribbles and outlines. His leg was shaking non-stop, and his mind was racing about all the ways his conversion could go with his history teacher. The final bell rang too soon, but he slowly packed his bag and talked to Charlie about what time he could come over her house to study for the upcoming test they had in Math.

Once they were the last people in class they made their way out the door and turned their separate ways. Dean walked slowly in the direction of Mr. Novak’s classroom and thought about what he was going to say, what lie he was going to come up with.

He knocked on the door to his history classroom and walked in. He scratched the back of his neck as he awkwardly stood in front of his teacher as he was grading papers. Mr. Novak coughed to clear his throat and took off his glasses to look up at Dean’s green eyes.

“Why were you drinking in school? You know that can get you suspended right?” Castiel snapped more hurtful than he meant it

“Yes, I know that, I’m sorry, I was just tired and I didn’t want to think, I didn’t drink the rest of the day though, I’m so sorry Mr. Novak.” Dean’s voice was shaking and he spoke so quickly it was nearly inaudible.

“I’m sorry for snapping, just know that you made a very reckless decision that could have gotten you in a lot of trouble. Don’t ever do it again.” He finished on a serious note. Dean played with the bottom of his sleeve nervously and Mr. Novak’s eyes followed. “What happened to your arm again? The truth this time please”

“Well, like I said I was cooking pancakes and bacon for dinner the other night and some grease splashed on me out of the pan” Dean responded, sounding more confident than earlier, giving more detail to his lie.

Castiel didn’t believe a word, “That’s strange, grease usually leaves smaller splattered burns, not one big one, unless there’s more?”

“No, it’s just the one little spot, nothing to worry about, it should heal up in a few days.” He quickly replied.

“Are you sure it was from bacon, Mr. Winchester?” Castiel looked at him intensely as if willing him to give him the real story.

As Dean opened his mouth the door opened, “Hey, Cas...” Ms. Master’s voice trailed off as both their heads snapped towards the open door.

“Hey Meg, what’s up?” Castiel asked as he moved towards her to talk in the hallway.

“I was just wondering if you wanted some coffee from the teacher’s lounge, but I see you’re busy,” she said with a suggestive smirk

“No I am not busy, I am trying to help, why are you like this?!” He sneered at his friend

“Whatever you say Clarence,” she almost sang and walked away laughing.

Castiel walked back into the classroom to see Dean sitting in his desk chair twirling around absent-mindedly, picking at something on his hand. “Dean,” he jumped out of his trance and looked at his teacher

“Oh shit, hey, sorry for sitting in your chair, and sorry again for swearing.” He was back to speaking very quickly.

“It’s okay Dean, nothing I’m not used to” Castiel chuckled. “Meg will be back in a minute with my coffee, then we’ll talk.” As if on queue she walked in with three cups of coffee shaking in her hand, she put down two on Cas’ desk.

“Cas, two creamers and three sugars. Dean, you seemed like the type to drink it black, but here’s two creams just in case” she threw them down on the desk he was standing at.

“Thank you very much, I really need a coffee to survive the rest of this day.” Dean said gratefully pulling a chair up to the desk.

Meg and Cas exchanged a short banter like good friends which made Dean smile. She left soon after she got there and Dean was left with his teacher, drinking coffee in silence. After his first sip he was so relieved he let out a short moan which made his eyes shoot open and he slowly looked at his teacher. Novak laughed and took another sip.

“How long have you and Ms. Masters been friends?” He asked casually in an attempt to make conversation.

“Well I started teaching here three years ago, we’ve been friends for the better park of two years”

“What about the first year?” Dean smiled with interest.

“Y’know people aren’t my favorite, it took me a little while to warm up to her. But we were both new, so it was easier to work together rather than against each other.”

“Huh, if you don’t like people why become a teacher? Is it the power trip?” He asked raising an eyebrow.

“No it is not the power trip. I love history and I want to share it with as many people as possible, I figured that teaching was the best way to do that.”

“Oh, that’s cool, I wanted to be a teacher when I was really young, but now I’m looking into mechanics. I work at Singer’s Auto Shop on West Main Street.” Dean was attempting to distract his teacher from the topic at hand.

“Good to know, will you give me a discount if I go there, my muffler has been making a funny sound.” Castiel quipped back.

“Of course, I’d do it for free if you gave me an A in your class” he said with a smile

“You already have an A in my class Dean” Novak sighed.

“Well, yeah that’s with studying and hard work” Dean laughed back. As he leaned forward to add a creamer into the rest of his coffee his ribs knocked against the desk and he winced.

“What was that?” Castiel asked very concerned.

“Nothing, I don’t know what you’re talking about.” He tried to cover up his stupid mistake. The creamer was dumped quickly into his coffee and he took a sip so he couldn’t say more.

“No, no, I saw that, what’s on your stomach Dean? Not another grease burn.” His eyebrows furrowed

“Actually, you know what they say, never cook bacon naked, I learned my lesson” Dean laughed brushing it off. “Why three sugars? You like your coffee sweet?” He tried, and failed to change the subject.

Castiel’s eyebrows didn’t budge. “Take off your shirt, let me see.”

“What??? No!” Dean exclaimed, pulling down on his sleeves again.

“Yes, you heard me. Take. It. Off.” The teacher enunciated every word.

“Why? You’re not going to find anything spectacular.” He tried playing it cool one more time.

“Dean this is not a joke, take off your shirt.”

Dean knew he wasn’t going to let this go so he stood up and started to unbutton the shirt. “Can’t you, like, get in trouble for something like this?” Dean questioned but his hands kept moving.

“I won’t get in trouble if I’m right about this.” He watched as Dean was finishing unbuttoning his shirt. 

He slid it off his arms and exposed his upper half. There were a few more of the same circular burn marks up and down his arms. There was a large bruise across his ribs that was yellowing, indicating it was a few days old. On his shoulder Cas could see a small cut that led to more on his back. He stood and walked around Dean like a predator stalking its prey. Inspecting his back which was also filled with scars, but they looked more like a whip, a belt. The teacher reached out instinctively to touch one of the old scars which made Dean’s entire body twitch with anxiety.

“Are you done yet? I’m cold, I’d like to put my shirt back on.” he said nonchalantly.

“Yes, you may redress, I’m sorry for touching you. May I ask what happened to you?” Castiel pushed carefully.

Dean put his shirt back on slowly, and he could feel his teacher’s eye on him. He remembered Charlie’s comment from earlier and he smirked as he looked up to lock eyes with the older man. Green met blue and Dean was not going to give out.

He responded slowly “I fall down the stairs a lot.” He tried his best to not sound sarcastic, but laughed at the end. Damn why did he have to be sooo funny. 

“Dean, you know this is no joking matter.” His teacher scolded him.

“I know it’s not a joke. I work two jobs and I’m almost 18. I just need a little more time, please, please don’t report my father.” Dean cracked and fell back into his chair looking broken and desperate.

“I am legally obliga-“

“I know you are that’s why I didn’t want to come here, but I trust you, I really do and I just need someone to be on my side, please” Dean cut him off and started begging. His voice was cracking and he was holding back tears.

“I’m on your side Dean, but I have to do something,” Cas trailed off walking over to the young man who had started crying. He placed his hands gently on Dean’s shoulders and repeated “I am on your side Dean, it’s okay.” 

After a minute or so of repeating this mantra that his student obviously needed to hear, he crouched down to place one of his hands under Dean’s chin and guide him so their eyes met. The green in his eyes sparkled from the soft tears that were still rolling down his cheeks. Castiel did his best to wipe them away with his thumb to no avail, but the tears didn’t seem to be sad or angry anymore.

“I’m sorry for crying, I’m not usually like this.” He said between sniffles. He grabbed a tissue off the teacher’s desk to blow his nose which made the other man laugh.

“What can I do to help Dean?” Castiel asked seriously, with his hand still on Dean’s cheek and his other resting on the boy's knee.

“You can keep this between us, I’ll do whatever you want, but I can’t have DCPS called, I really can’t.” Dean said wiping away the last of his tears and giving both his hands over to Cas. Dean liked that nickname for his seemingly stiff teacher, more fun than his usual demeanor.

“What if we meet once a week after school to talk? Fridays maybe?” Castiel suggested while rubbing his hands across the younger boy’s thumbs.

“Friday’s should work for me. What kind of things would we talk about?” Dean asked innocently.

Castiel chuckled and replied softly, “Anything you want Dean. I just want to be here for you.” With those words out in the open Dean visibly relaxed.

Just so you know I have to pick up my little brother at 4:30 every Friday.” The younger boy interjected quickly, tensing up. Dropping his teachers hands in his lap and scratching the back of his neck. He couldn’t believe he had let his guard down.

“How old is your brother?” Castiel responded evenly not giving up on his quest to get his student to open up.

“Uhh, he’s 13, graduating middle school this year,” Dean laughed lightly. “I can’t wait to bully him all of next year.”

That makes it click for Castiel; Dean is just a child. He displays himself as this big bad baseball player, but he’s just a goofy kid who loves his brother. Clearly forced to grow up too fast, Castiel remembers seeing a form saying that his mother died in a fire when he was young. His student obviously feels the need to protect his younger brother from everything that might hurt him, especially their father.

“I’m sure he’ll appreciate that.” Cas laughed back.

“Hey, sorry for lying to you earlier, I just always have to look over my shoulder, y’know?”

“Don’t worry about it kid, you have every right to protect what you love.” Castiel smiled at him endearingly.

Dean pulled out his phone to check the time and it was already 3:30, and he was supposed to meet Charlie at 3:45.

“I’m sorry Cas, I mean, Mr. Novak, I have to go. Charlie and I are studying for a test we have next week. I’ll see you next Friday?” Dean was whirring around the room toward the door with his backpack over his shoulder in a flash. He said a final goodbye and left. Castiel barely had time to react to the situation before Dean was gone, he mumbled a ‘bye’ to the closed door of his classroom and went back to whatever he was doing before Dean walked in. He did have to admit, he liked the sound of Meg’s nickname hanging off Dean’s lips, even if it was just a slip up.


	2. The Family

**Summary for the Chapter:**

> This one basically gives a bunch of background. Gives Charlie some depth and John. Start to see Dean and Sam's relationship, which we love. Dean is a good guy and I love him. Dean goes to work.... one of three jobs.

Dean was rethinking the entire situation that happened after school as he walked up to Charlie’s door. He knocked and felt calm for the first time in weeks. A few moments later the door swung open to a nervous looking Charlie startling the boy out of his haze. He just gave her a knowing nod and she visibly relaxed, but didn’t notice she was still in front of the door.

“Ahh, the great Charlie Bradbury speechless at the likes of me? This is one for the books.” Dean taunted as he pushed past her. This house felt like home to him, more home than his house where his father lived.

“As if! Don’t worry you won’t catch me caring about you again!” She huffed. “What time do you have to leave?”

“Uh, Sam has practice until 6:30, I have to pick him up and be home by seven.” He quietly thought out loud.

“All right! Then let’s get to studying!” Charlie exclaimed, voice dripping with sarcasm.

They sat down and started with the Calculus section of their practice packet, cross checking answers every so often. After a while Dean’s mind started to wander to Sam, then to Cas, then to his father. His dad wasn’t always this way, he barely remembered life before his mom died; but, he knew they were happy. He knew his dad was definitely not a raging alcoholic when Mary was still alive. When Dean was young John had told him stories about how he was raised as an army brat always moving around. His parents always wanted him to be in the Navy, ‘carry on the family tradition,’ even if that’s not what John had wanted. Since John was discharged he and Mary promised to be different and love their children and support them unconditionally, which was derailed by Mary’s death. After Dean’s mom passed in the fire, it was as if all the pent up rage, pain, and trauma caught up to him. Dean couldn’t recall the last time that his dad was sober, but he couldn’t blame him, he was in pain, his wife died, he had PTSD. /No! Dean had to stop making excuses for his abusive alcoholic father. He lost Mary too, he has had to single handedly raise his baby brother and protect him from their father./

A loud growl from his stomach snapped him back to reality and Charlie snorted with laughter. “You wanna take a pizza break?” She said in between laughs.

“That sounds good, it wasn’t that funny though I didn’t have lunch! Sam took the rest of the bread for his sandwich!” Dean argued. He checked his watch to make sure he would have enough time to eat and pick up his little brother on time; the watch read 5:15.

He nodded again as Charlie walked over to the bottom of her stairs and yelled up to her mom, “HEY MA! YOU WANT SOME PIZZA??”

Dean got up and walked into the kitchen, his friend’s voice fading out of range. He knew this house like the back of his hand. They met in the first grade when Dean spilled his PB&J all over her ‘123 Book.’ She was so mad he could have sworn her head was going to pop off, but their teacher, Mr. Henriksen cooled her off with a more interesting book. At recess that day she pushed him into the wood chips and they laughed it all off. As long as Dean can remember he has loved making Charlie laugh, it made him happy, calm. After that fateful day at recess Dean was pretty much in the Bradbury house every week, he used any excuse to not be at home, he even brought Sammy around as he got older. 

Charlie and Dean knew virtually everything about each other. Sadly he knew her dad when he was still around. When Charlie’s mom got diagnosed with breast cancer he couldn’t get out the door fast enough, leaving an 11-year-old Charlie to care for her mother and herself. These past few months had been especially hard with Mrs. Bradbury on bed-rest. She was due for a double mastectomy in a few weeks to hopefully get rid of the cancer for good.

Once his red-headed friend finished yelling to her mom about what kind of pizza they were getting she found Dean in the kitchen getting plates and a tray for her mom.

“It’s times like these I wish I was straight” She moped, coming around the large wooden table to hug her best friend. He laughed and grabbed his phone to order.

“What kind of pizza did you guys agree on?” He asked resting his head on top of hers. She seemed so small, so vulnerable when she was hugging him like this, he didn’t really want her to stop.

“Bacon and cheese” she replied into his chest-shoulder-area.

The phone rang and he ordered quickly, holding onto Charlie tightly the whole time. Dean held Charlie tight even after he had ordered. They stayed like that for a while, just breathing each other in, in the silence. They lost track of time and the doorbell rang, signifying they had been there for 15-20 minutes, and they jumped out of each other’s arms as if they had been caught doing something wrong. Charlie left the kitchen to go grab the door leaving Dean to space out and get lost in his thoughts, something that seemed to be happening a lot today. His body slouched at the loss of warmth from his best friend. Charlie returned to the kitchen a few minutes later to a dazed Dean looking at the table. 

“Earth to Dean, are you in there?” She asked, waving her hand in front of his eyes. He cracked a smile and looked up at her with bright green eyes.

“You wanna eat with your mom?” He offered.

“Yeah, that would be nice.” She grabbed the pizza boxes off of the table and Dean grabbed the tray and plates he had set out earlier. She smiled at him and walked up stairs with him in toe.

“Hey mom,” Charlie said, knocking on the door lightly before pushing it open. “Is it okay if we eat with you?”

“Of course baby,” She responded smiling warmly at her daughter. Dean smiled and waved as he poked his head out from behind Charlie. “I swear you get taller every time I see you.” 

“You should see Sammy, he’s going to be taller than me soon enough.” Dean laughed setting down the tray as she sat herself up in bed.

“Thank you sweetie” she chimed. 

They sat and chatted about school, girls, boys, and life. By the time that they were all full there was one piece of bacon and two slices of cheese.

“Can I take these for Sam?” Dean asked kindly, swallowing his last bite of crust. He had been checking his watch periodically for the last 20 minuet while they ate. He figured he had to leave the Bradbury’s by 6, 6:10 at the latest to get to the middle school on time and back home before John had to take the car, to the bar of course. 

“Oh yeah,” Charlie cut into his thoughts.

“All right, thank you, I should get going soon,” Dean said nervously even though he knew there was nothing to be nervous about. He was safe here, no risk of someone losing their temper over something so insignificant. “I’ll see you soon Mrs. B,” Dean said, flashing a quick smile as he rose to leave. Charlie stood with him to give him a quick hug goodbye.

“Text me later, will you?”

“I have work tonight, so it will probably be late.”

“That’s okay, as long as I know you’re safe.” She sighed

“Yes ma’am,” He said smiling again as his usual facade came over him. 

He left and started his car quickly and turned left towards the middle school. Metallica blasted through the 1967 Chevy Impala and Dean let a smile rest on his face as he rolled the windows down. He knew this would nearly embarrass his little brother to death. His left arm hung out the window and he laughed to himself.

When he pulled up to the school he saw a few kids with his brother walking off the field. He instantly turned the music even louder and honked to get his brother’s friends attention. Sam hung his head as they all burst into laughter, he glared at Dean and his friends patted his back as he walked away. He didn’t look at Dean when he got in the car, he looked solemnly out the window until they were about a quarter mile down the road. Even then the look on Sam’s face could kill, but it only made Dean break out into another fit of giggles, his mission was a success. After he had finished he absentmindedly hummed along to whatever Metallica song was playing.

Sam finally broke his silence by saying “Why are you like this?” Unknowingly repeating Charlie’s words from earlier. “You’re almost 18!! I am almost in high school! Your antics aren’t cute anymore.” His little brother complained.

“I think I’m adorable.” Dean flashed a wide smile over to the passenger seat. Sam didn’t lighten up on his - what Dean liked to call - bitchface. “C’mon Sammy it was a harmless prank” Dean signed, feeling an inkling of guilt. “I’m sorry, okay?” He finally gave into what Sam wanted.

“Good!” Sam retorted quickly, facing Dean fully and giving him a smug little smirk.

“Whatever, Bitch”

“Jerk”

Dean reached into the backseat and pulled out the pizza he brought for Sam, who happily took it. Dean laughed as Sam shoved his face with pizza. His brother looked at him and asked “What?” with a mouthful of cheese pizza. This only made Dean laugh harder.

He eventually sobered up from his laughter when Sam gave one of his patented ‘bitch-faces.’ “What are your plans for the night?”

“Uh, I have some homework and then I was going to watch a movie or something, maybe have a friend pick me up?”

“Alright, I have to work tonight, I’m dropping you off and I will be grabbing my stuff to head out as soon as possible.” Dean sighed, “Will you be okay alone?”

Sam thought about it for a minute while he was finishing chewing. “Yeah I should be fine, I’ll probably have Amy or someone pick me up.”

“You like her?” Dean said suggestively.

“Ew! NO!” Sam exclaimed. “She’s just a /friend/ we like to go on adventures together, that’s all.”

“Okayyyy whatever you say Sammy!”

“It’s /Sam/” the younger boy huffed.

Dean turned up the music “Sorry, what was that I couldn’t hear you!” He cackled again.

They sat in comfortable silence as Sam finished his pizza and Dean sang along to the booming music. As they neared the house he lowered the music and gave sam a knowing glance. A look that said ‘get in, get out.’ In the drive way Dean shut off the car and they both took deep breaths before they got out of the car. As soon as they got to the door, Dean instinctively puts himself in front of Sam, expecting the worst. 

John was waiting for them in the living room, in his leather recliner. He was in front of the T.V. with the remote in his hand, flipping through channels. When the door closed he looked up and scoffed at the slightly nervous look on his son's faces. He rose and held his hand out for the keys. Dean took them out of his pocket and placed them in his hand, he smelled like cigarette smoke and gasoline.

“I’ll be back later.” John grunted as he took the keys and headed for the door.

“See you later dad.” Dean said sadly when he heard the engine rev.

He turned to Sam and punched his shoulder playfully. “What are you lookin’ at?”

“Nothing much,” the younger quipped.

“Alright slugger” Dean laughed it off. “Imma go get ready for work and I’ll be gone until two, if anything goes wrong call me, if I don’t pick up, call the RoadHouse.”

“Dean, I know the drill, I’m probably going to end up sleeping over at my friend Alfie’s house. Will you pick me up tomorrow after work?”

“Yeah, I’ll just need an address, I get off of work at 8am, let me know what time you want to get picked up because if I can I’ll go home to get some sleep for a little.”

“Dean what did I tell you about overworking yourself?” Sam sighed at his older brother.

“Sammy, don’t you worry about me, It’s the weekend, I’ll go out and be normal tomorrow night, I have off.” He rolled his eyes at his overprotective younger brother.

“Listen, I’m just looking out for you, I love you.”

“Yeah yeah, I love you too, now go get some homework done.”

“Yes sir!” Sam mocked, but turned to go up to his room.

Dean looked at the clock over the kitchen sink, it read 6:50. He had an hour before he had to go over to The Road House. The sink was lined with beer bottles, so he pulled out the recycling bin and started piling them in. He loaded the dishwasher and ran it before grabbing himself a coke out of the fridge and sitting down on the couch. He looked around the room looking for any sign of Sam. Flipping through the channels until he landed on a guilty pleasure, Dr. Sexy. Sam always made fun of him for watching it, but it was just so damn good.

After one episode it was time for Dean to head out. “Bye Sammy!” He yelled up the stairs.

“BYE!” He heard a distracted shout back.

He double and triple checked to make sure that he had everything before he grabbed his helmet to head to work. Keys, wallet, jacket, diner uniform, chopstick(yeah he wears chapstick), helmet. He had everything. Outside it was a little colder than he was expecting because night was starting to fall, the sun warms everything up, imagine that. Throwing on his helmet he lifted the seat to load everything else he needed in there. He jumped on and revved the engine before peeling out of the small driveway.

The Roadhouse was thankfully only 15 minutes away from their house. He was bartending tonight, because Ellen, the owner, had been training him since he was fifteen years old and screw any law that said he couldn’t handle alcohol. Dean had always known Ellen, since he was about six years old, when John took the boys to bars because he couldn’t leave them at home yet. Ellen’s daughter, Jo, and Dean would fight like brother and sister when they were younger, but as they grew up together they just became family. Jo was two years younger than Dean, but was fiery as a pistol. She was one of the toughest people Dean knew, maybe he just had a thing for having powerful women in his life. 

The wind whipping past his jacket had calmed him since he started riding two years ago, he figured a bike was cheaper than a car so he better learn how to ride. It calmed him to be riding. He was in control when he was driving, he liked being in control wherever he could get it, that’s why he loved being the captain of the football team and the lacrosse team. He had a handle on his players and himself when he was in the game.

One more left turn when he was there, he slowed down to really take in the moment. He felt free. A smile spread across his face in the cold night air. He checked his watch for the third time that night and he pulled out back to park with the rest of his co-workers. I hope Ash is on tonight, Dean thought to himself. He took a deep breath before hopping off his bike, thanking whatever God there was that the Impala wasn’t there, but there was a funny looking pimpmobile in the parking lot out front.

His bike locked up and forgotten as the smell of burgers took over Dean’s nostrils. He couldn’t wait for his shift meal, granted that was at 11, which was three hours from now. Grabbed a card and clocked in on the old machine which clicked and wrote his arrival time on it, 7:45 PM. It didn’t take long for Ellen to notice him walking over to the bar.

“What’s up kid?”

“Oh, you know, the usual,” he laughed nervously “where do you want me tonight?”

“Uhh, well a few tables just came in, I’ve been working the bar, Ash and Jo are on the floor. Why don’t you grab section one the new tables sat over there.”

“Sounds good boss!” Dean whirred away to Ash and Jo letting them know he was picking up tables one through four.

The first table he went over to, he got their drink and appetizer orders and wrote them down in his little green notepad. He wanted to hit at least one more table before heading back to the bar. Table two didn’t even have menus so he assumed they were new, he saw a cute brunette on one side of the booth, but when he got to the table he almost choked.

His teacher’s blue eyes looked up at him and the air escaped his lungs. His hair was not gelled in place like usual, it was messy and cute. His usual trench coat lay beside him on the bench, but instead of a button-up and tie he was wearing a tight black t-shirt. The jeans caught him completely by surprise though, Dean completely forgot he was working and not scoping out someone to hook up with.

**Notes for the Chapter:**

> Every chapter from here on out will hopefully be about 3,000 words give or take. Let me know which way you guys think I should take this. I have many ideas, maybe you guys could help.


	3. Work Work Work

**Summary for the Chapter:**

> Dean goes to work, and guess who's there ;)))
> 
> Dean works two jobs and makes a few new friends!!
> 
> Also a little bit of sexie times so beware of that. I'm bad at summaries, but this day is finally over

The cute brunette man in the booth laughed at Dean’s change in demeanor.

“Hey cutie, are ya here to take our orders?” He asked with a devilish smile.

“Yes I am! I’m Dean and I’ll be your server tonight.” He snapped back into it and he smiled. “What can I get you two gentlemen tonight? Starting with drinks and appetizers? Just drinks?”

“Uhhh,” Castiel still hadn’t collected himself enough to answer. 

“We’re going to do both.” The other man chimed in.

“Of course! What can I get for you guys tonight?” Dean asked cheerfully.

“I’ll take a … whatever the fruitiest drink you can think of is, and my speechless brother over there will take a double scotch neat, top shelf, well aged..” The man across from his teacher responded with the same pep in his voice. Dean was just the tiniest bit relived that this cute brunette was related to Mr. Novak and was not his date. Partially because he thought both men were ridiculously attractive but also when he walked over, there was a pang of jealousy in the back of his mind.

“I make a really good Malibu Sunset, I think that’s the fruitiest thing I can think of. And we have a single malt Johnny Walker 30 years, will that do?” He winked and smiled.

“Sounds great, what do you have for appetizers?” Castiel finally chimed in.

Dean had to will his head to turn and meet those glaring blue eyes that scared him half to death just earlier today. He did it anyway and smiled politely. “We have mozzarella sticks, nachos, a new special boneless wings — which are just chicken nuggets with sauce, quesadillas, and we have a few homemade soups.”

The two men pondered for a minute. “We’ll have mozzarella sticks, aaaaand nachos please, make sure there’s extra sour cream please.” Castiel piped up.

“What if I want to get a quesadilla?!” His brother quickly responded.

“Oh hush up, you’ll be fine with nachos, it basically a quesadilla with hard tortillas.”

“Alright, drinks coming up and I’ll go put in your order for nachos and mozzarella sticks.” Dean cut into the banter that was about to take place. Once he walked away he took a deep breath. Somehow he knew this was going to be a long night for him.

Behind the bar felt natural to Dean, plus when he looked up he could see into the booth his teacher and his ridiculously attractive brother were sitting at. Dean would be lying if he said he hadn’t thought about his teacher in that way before, but the way his slacks fit him and his button-up shirt fell right into Dean’s schoolgirl fantasies. He made the drinks with ease, something he’s done since he was a kid, but he loved it. It was like holding the thing that ruined his life gave him control, which he loved.

The scotch in one hand and this bright fruity drink in the other. He steadied his breath and walked back over to the table. As he walked up he heard low voices in conversation and they muted when he got to the table. He put their drinks down respectively and turned to walk away.

Dean heard what sounded like a kick to the shin and Castiel yell an “ow!” 

“Dean wait,” Castiel called and motioned with his hand when the younger boy turned around.

“What can I help you with guys?”

“Dean, this is my brother Gabriel.” Castiel said rolling his eyes. He wondered why the teacher was doing this.

“Hi Dean! My baby brother here was telling me how you’re his student?” The brunette who now had a name asked him this seemingly simple question, yet he felt like there was a trick or a trap or something.

“Uhh, yeah I am, I’m a junior and I’m in his US History class. I was thinking about doing taking his military weapons class next year.” Dean scratched the back of his neck. He remembered the bruising on his stomach when he felt a quick pinch and put his arm back down quickly. Dean was not planning on running into anyone he knew here tonight. 

“Oh that’s cute, you like the way he teaches because he won’t tell me if he’s good at his job. Too modest or something” Gabriel chuckled, something he seemed to be doing a lot of.

“Yeah, everyone really likes him, better him than Mr. Morningstar, he’s the devil.” Dean rolled his eyes and relaxed his stance, leaning into the conversation. 

“That’s good, we wouldn’t want a bad teacher over here.” He pointed his thumb suggestively across the booth.

“So,, Gabriel, why’d you want me over here?” Dean asked after a quick laugh and a dip in the conversation.

“Ugh, please, it’s Gabe, and I was wondering how someone that’s so young can be so good at making drinks?” He asked winking and giving him a dumb, doe-eyed face.

“Oh, well, uh, Gabe, I grew up in bars, and not in a good way, so I picked things up and I’ve been here for years.” 

He moved his arms out in front of him for them to see his scars, feeling not so ashamed all of a sudden. This was his territory and there was nothing his teacher could do. But when he looked over there was this sad, worried look on Castiel’s face, he couldn’t help but but his arms behind his back.

Both men were silent for a little too long and just kind of looked at Dean in awe or terror, either way, Dean was working. He walked over to one of the other tables he was supposed to be taking care of, every so often looking over his shoulder to the booth in the corner. They were laughing and smiling and Dean was working hard.

The bell in the kitchen rang loud and clear and he went back there to grab the food. Of course it just had to be nachos and mozzarella sticks for table two.

He brought them over, terrified for the awkward conversation that he knew would ensue. “Here you guys go! Extra sour cream just for you guys” Dean smiled and winked at the two men.

“Thanks Dean-o” Gabriel responded before he could even think about it.

“Dean…o” Castiel looked at his brother like he had two heads.

“Listen, I’m sorry it just came out” he laughed nervously

“It’s fine y’all no big deal, it was kinda cute if anything!” He smiled charmingly.

“You’re tooooo cute I could literally eat you up” Gabe licked his lips.

Dean laughed and blushed at the words. He then heard a loud thud under the table which must have been Castiel’s retaliation from earlier.

“Is everything okay? With the food I mean- Can I get you guys more drinks?”

“Yes please, more drinks, Dean. Keep them coming until you leave.” Castiel cut into whatever Gabe’s drunken head was going to say.

“Sounds good to me!”

The rest of Dean’s shift went pretty smoothly, he had a bunch of regulars that he knew and loved. Around ten o’clock it the food orders slowed down significantly and they started to clean up the kitchen. Ellen thought it was appropriate to leave, she trusted everyone else here to close up properly. She took Dean off the floor and stuck him behind the bar, but he told Ash and Jo that he would keep an eye on table two.

Every time he went over there to refill their drinks they got a little more forward. Gabe would say some flirtatious comment and Castiel would immediately shut him down. Every time Dean thought his teacher’s name he became more comfortable with it, so much so he started calling him Cas in his head. Since he heard Ms. Masters say it to him so casually he couldn’t help but like it too. Cas was harsh to his brother, it was sweet, almost like he was protecting Dean. Dean didn’t need to be protected, but he came off that way after school, breaking down and everything. 

When his teacher said that he was on his side he couldn’t help but feel different, like he finally had someone who understood and didn’t judge. Someone who he could really trust and talk to on a regular basis, almost like he had a new friend. It would take a while, but Dean knew this was the start of something important. Dean often found that Cas would look at him behind the bar. He wasn’t sure if it was because he was worried or something else, but he just kept bringing them drinks anyway.

At around 12:30 Dean decided that the two men had enough to drink. While he liked having them there and the rest of the place had died down, he knew that them staying any longer would go against his good conscience. He called them an Uber, gave them their last round of drinks, and the check — which against his better judgement he left his phone number on. He wrote “let me know when you’re home safe” on it. 

Dean placed their check down at about 12:45 AM. He said “Your cab is going to be here in about 10 minutes. I would finish your drinks and go home.” And walked away before either of them had seen his phone number. He watched them carefully as they gave Jo the card and struggled to get up. They looked over to Dean a few times, but he trusted that they knew he was just worried about them. Once the card came back they left and the door slammed shut behind them in the fall wind.

Just like that they were gone. Dean settled in for the night. He grabbed a bunch of napkins and silverware. He sent Ash on his way home for the night. Jo was manning the bar with a few people around at tables and bar stools. Dean was handling all the side work. He filled everything in the fridge and took out the trash before returning to the bar to roll silverware for tomorrow. The clock read 1 before he knew it, closing time.

Jo started to close out all the remaining tabs and close out the register while Dean wrapped up his tasks and started packing up to leave. All there was left to do was wipe the bar, shut the lights off and lock up. He grabbed his keys and helmet to bid Jo a goodbye. 

“I’m good to go right?” Dean asked already knowing the answer

“Oh yeah, thanks for staying to do the side work” Jo said over her shoulder. 

Before he left the Road House Dean checked his phone to find a text from his brother:

Sammy [hey, just pick me up from Alfie’s house after you get out of work, whenever that is.]  
The address was attached below his text.

He shot him a text back:  
Dean [Hey! Just saw this, I’m getting off work at 8:30, just so you know, I’ll be there around 9 then] 

Night was his favorite time to ride. Everything was calm and quiet. He had to ride 20 minutes to his other job and it was always better to be early. The roads were all but clear at 1 in the morning so he made it to the Diner before 1:30 which was nice because that meant he could take a quick power nap in the office. The only downside to working the graveyard shift on the weekends was all the kids that he knew coming in from parties.

Tonight the drunk kids that he knew unfortunately were from the football team, including Benny. There were also a few cheerleaders with them. Clearly they had won tonight and they were out celebrating. One of the last people to walk in was his ex, Lisa. They still had something, but when she walked in his stomach dropped. Benny was sitting at the booth behind her with a bunch of guys.

Dean really wanted this night to be over. His stupid little uniform looked especially stupid right now as he walked over to his friends. Lisa had ended up on one of his teammates laps and that made him undeniably jealous. Benny however could not keep his eyes off Dean.

At around 3:45 Benny had followed Dean into the bathroom and locked the door behind them. He immediately made a move on Dean and started kissing him. There was no response at first but Dean eventually gave in. Benny was kissing him with need and lust. It was all tongue and teeth, until he moved away from Dean’s mouth and down to his neck which made Dean forget that he was at work.

“Benny, Benny, Benny. Slow down, you’re drunk.”

“Hmm, nah tha drunk, still know I wan’ ya” Benny barely got the words out before going back to kissing Dean and pushing him up on the sink.

“Ugh, Benny” Dean all but moaned as Benny unzipped his work slacks.

After unbuttoning his shirt the drunk boy kissed down Deans freckled chest to his hardening member. Dean bit back a moan and there was a deafening knock on the door interrupting their moment.

“Fuck,” Dean swore.

He jumped off the sink and pulled Benny into a stall. He buttoned his shirt and zipped his pants before opening the door to Crowley, the former captain of the football team, a senior. 

“Get your guy under control man, he could barely get into the stall by himself.” Dean snapped at his teammate before making his way out of the bathroom.

“Oi, don’t tell me what to do, he can handle himself” Crowley snapped back.

“Doesn’t seem like it,” Dean said as Benny started to vomit into the toilet. He laughed and then got back to work.

It wasn’t long after that, that they all packed up and left. At least they tipped well, Dean thought to himself that Lisa probably had something to do with that. She hung back behind the other cheer leaders to say goodbye to him personally. She looked a little sad, like she knew what was happening to Dean, like she knew that he was so lost at the moment and just kept going anyway.

Once the teens were gone there was limited business as usual, a few families stopping for a bite to eat on a vacation of some sort, then the few homeless people looking for some water and warmth. Dean was more than familiar with a few of the homeless guys, they came by the Road House earlier in the night and then come here early in the morning.

At around 6 in the morning the early birds started rolling in. They had a special from 6-8: four pancakes with three strips of bacon, two scrambled eggs, and one piece of toast with any drink, all for the low price of $12. 

For a minute when he had nothing to do Dean checked his phone and he had two texts from numbers he didn’t have saved.

(816) 493-2722 [hom safe deeeen] 

(785) 809-0807 [we gottt home saf - Cas] 

He laughed and saved their numbers in his phone. He had almost completely forgotten how long of a day he had, but then those texts took him right back to when he was crying in his teacher’s arms. /It’s almost 8, it’s almost 8, it’s almost 8/. Dean kept repeating to himself, he couldn’t wait to go pick up Sam, his bed sounded /so/ good right now.

“Hey Dean!” His co-worker who usually works the graveyard with him said, startling him out of his daze.

“Hey Dorothy! Tonight wasn’t too bad we made like $100 each in tips!” Dean said excitedly. “But I cannot wait to get off.”

“Yeah, I’m pretty wiped too!” She was always so nice, maybe Dean should talk to her more often.

“You got any plans for the day?” 

“Oh yeah, big plans that involve me getting in my bed with my weighted blanket for at /least/ 8 hours.”

“I feel that, I have to pick up my little brother from a sleepover and then I’m headed straight to my bed for sure.” Dean laughed.

“What was up with those guys earlier? The whole bathroom situation?” Dorothy inquired, trying not to be too pushy.

“Oh well, I, uh, kinda have a thing with one of them and he came onto me in the bathroom, but I pushed him off because he smelled like…” Dean looked around and lowered his voice “alcohol. Anyway he ended up yuking it out in one of the stalls, but this guy that used to be captain has beef with me because I ’stole his position’ or something, anyway he was annoyed that the door was locked.” Dean found himself being completely honest with her.

“Wow, that sucks, I’m kind of glad I graduated high school in the spring, it just sucked, all the drama and everything. At least our school is diverse in sexuality, nobody really cares right?”

“Oh shoot, yeah I forgot you went to Lawrence High” 

“Yeah, what sports do you play other than football?”

They carried on their conversation for a little while in-between taking care of customers. Dean found out that he actually kind of liked this Dorothy girl. He was excited to tell someone about her, a new friend that no one else knew! He asked her questions, found out that her father was a writer and her mother absolutely loved the story of “The Wizard of Oz” hence her name. They also discussed LARPing because Dean would never admit that he loved it when Charlie dragged him along, that would be the end of his popularity. Casual conversation that made the time pass.

8 o’clock rolled around a lot faster than he thought it would and Dean found himself sad that he had to leave his new friend. Wow, two new friends in two days, that has to be some kind of record for Dean. He started to do all his side work so he could leave a few minutes early.

“I’m sorry I have to go get my brother now, it was actually so fun talking to you.” Dean flashed her a wide, genuine grin and laughed. “I can’t believe I’ve been here since May and we haven’t talked this much.”

She had really pretty hazel eyes, he noticed when she blushed and laughed nervously. “I was always afraid to talk to you. You seemed like this big scary guy, but I see now that you’re just as normal as the rest of us.”

“You were scared to talk to me? That’s funny, I was always nervous to initiate a conversation because you had to train me when I got here.” They laughed together for a little bit after that.

“Do you need anything or am I good to clock out? [fill in later, girl who traveled from another dimension] just got here.”

“Yeah, you’re good to go, I’ll see you soon?”

“Oh yeah!!” He grabbed a napkin and a pen from the desk. “Here’s my number, text me anytime.” He smiled proud of his confidence. With that he grabbed his stuff and headed out to the parking lot.

Even with his helmet in hand he managed to forget that he just had his bike on him and not Baby. Sam would have to suck it up. Alfie’s house wasn’t too far away from theirs, 20 minutes at the most. Either way, he had no other options because he wasn’t going to go out of his way for his baby brother. 

He sent a text to Sam before he left.  
Dean [on my way, be ready] 8:15 am

Dean then hopped on his bike and peeled out of the parking lot. He ran into some traffic on the way through town, but it was nothing major. He got there at 8:45. He called Sam, but he must have heard the roar of the bikes engine. He came out with an annoyed look on his face. Dean took the keys out.

“Look, I’m sorry, I know its not preferable but I didn’t want to go all the way home and deal with John before coming here. I’m exhausted, please cut me some slack Sammy.” Dean sighed looking defeated.

“Alright, whatever I’l let you slide this time.” The younger brother sighed.

Dean gave him the helmet to which Sam grimaced again.

“Listen you don’t have to like it but you do have to wear it. I refuse to let you get hurt, especially on my bike.” Dean set him straight and he put it on. Dean got on first and Sam hopped on the back.

“This is so embarrassing” he hissed under his breath. Luckily his voice was drowned out by the engine revving. They took off down the road and back towards their house.

**Notes for the Chapter:**

> LMK how y'all liked it, I worked soooo hard on it 😘 This chapter actually took a really long time haha.
> 
> Y'all I lied, I have so much college work to do this week the chapter will probably be up on Friday or Saturday so that I don't flunk out.
> 
> Thank you for understandingggg ❤️


	4. Let's Party

**Summary for the Chapter:**

> This one is pretty good. It does have a SEXY scene so beware if you don't want that. Dean goes to work and get's a surprise visitor and then he goes to a party and has more fun than expected.

**Notes for the Chapter:**

> DO NOT DRINK AND DRIVE!!! Guy's I'm so so so sorry this took so long to get out, my projects are not going well. Let me know how you guys feel about this one. Thank you for being patient.

When Dean woke up it was around 5. He made a system for himself on weekends that he had to work. 8 hours of sleep. Maybe 8-and-a-half if he was lucky. Today was not one of those days. His alarm went off and he paid no mind, but just a few minutes later there was a loud slam of the front door. He was on his feet in seconds to check Sam’s room. When his little brother wasn’t there his stomach dropped. 

Panic set in when the bathroom was empty too. Dean rushed down the stairs to find a drunk John stumbling in the kitchen to get another beer. He knew his father had to drive home in the car which made him irrationally angry. He continued looking around the house for Sam, but only came upon empty rooms. 

He walked out the back door to catch his breath. There was his brother working on some random soccer drills in their fenced in backyard. Sam must have heard the door close because he looked up at Dean. The worried look on his face gave everything away… John was home. They both walked inside, Sam instinctually tucked behind Dean. 

“Hey dad!” Dean started. “Sam has a soccer game tonight. Is it okay if we borrow the car?”

John was rooting through the fridge and looked up. He mumbled something under his breath.

“Was that a yes?” Dean prodded carefully.

“Yeh.” Their father grunted loud enough for the brothers to hear. 

“Okay! We’ll be out of your hair for the rest of the night then!” Dean pepped up.

“Whatever,” the older man ended the conversation.

Sam packed a change of clothes and a small blanket in his duffel bag. Dean threw on a black t-shirt and some old jeans. He grabbed the keys and called for his brother. Sam came trotting down the stairs with his unusually long arms and legs covered by his soccer jersey and shorts. This kid was going to be taller than Dean soon enough. His hair was short and he had goofy looking bangs. He was stupid smart and nerdy, but that was his Sammy and he would never get tired of him.

“Ready?”

“Yep, let’s go.”

They left the house without looking back. Dean could not wait until he left that house for the last time. He would miss the memories of his mother, but they had been drowned out by the years of beatings. All that was really left of Mary were pictures and old jewelry. The house smelled like John, which consisted of cigarettes and Jack Daniels, sometimes beer. It was no longer his home, home was someplace you felt safe and that was not his childhood house in Lawrence Kansas.

Sam closed the trunk and hopped in the passenger seat as Dean started the car. His leather jacket lay in the seat between them. 

“You got everything? We won’t be home until tomorrow.”

“Yeah, I got everything.” Sam sighed with a twinge of sadness.

The engine rolled over and Dean backed out of the driveway. The soccer game started at 7 so Dean watched them warm up for around an hour. He even kicked the ball around before everyone got there. While Dean hated lying to Sam, he usually did it so his little brother wouldn’t worry about him. He had work at eight, but there was definitely a party that he would be going to after. Benny had texted him about a get together at Crowley’s house. As awful as he and his mother were, they had money and lots of it.

Dean was always and always would be in the front row cheering his little brother on. Sammy was center forward which dean only knew because he told him for days after he got the position. As annoyed as he was, he was even more proud. When Sam scored the first goal Dean was on his feet screaming at the top of his lungs. His brother looked over and smiled trying to be humble. Sam’s happiness was the only thing that ever mattered to Dean. Even if he had to work every night til he dropped. His brother deserved the world and Dean would do near anything to give it to him.

Before he knew it his watch read 7:30pm. He disappeared without a trace in the crowd. When he got to the car he sent Sam a quick text to his brother to read after the game.

7:40 pm  
Dean [Hey, sorry I had to go. You did great!]  
Though he would never admit to anyone he always uses exclamation points in texts with his brother because he loved him.

He hopped in the car and headed to work. To his surprise it was very busy when he got there. He jumped right in behind the bar, because tonight Ellen couldn’t come in: she had a date which she refused to talk about with Dean or Jo. He quickly scanned the large dining room for John, thankfully he came up blank. After throwing on his “Roadhouse” shirt he was already making drinks.

Time flew by with the constant drink orders coming through and all the orders to be taken at the bar. He didn’t stop working for even a minute until about 12:30 in the morning and that was only because it was last call. 

The bell on the door rang and Dean looked up to turn whoever it was away, until he saw an all-too-familiar trench coat. Dean’s mouth dropped open for half a second until Cas’s eyes found him. He walked towards him with a purpose and cracked a smile as he did so. The eye contact never broke and they finally met, separated only by the bar. The teacher's hair was a mess and it looked ridiculously attractive, Dean wanted to reach out and run his fingers through it. He was wearing another plain t-shirt, but this one was red, and tonight his jeans weren’t ripped, just a little worn down.

“Hey, you looking for a drink two nights in a row?” Dean asked with a casual smirk.

“No, please, no more alcohol.” Cas sighed. “I came here to apologize for last night.”

“Why would you want to apologize? You guys were so much fun and tipped me REALLY well.”

“Well, we were very intoxicated, and you are my student, and you have my phone number now which is highly inappropriate. I would like to apologize for being belligerent and anything my brother or I might have said to you that was disturbing or vulgar.” The older man responded quickly.

“Well ya have absolutely nothing to apologize for. I can even delete your phone number if you want?” Dean said to calm him down.

“Are you sure, Dean? I don’t want to make you uncomfortable.”

“Hell yeah I’m sure, you didn’t do anything wrong. I’m definitely keeping your brother’s number, how old is he?”

“Oh my goodness, he is five years my senior.”

“And how old are you?” Dean felt like he was flirting but it was his teacher, he couldn’t be flirting, could he?

“I am twenty-six, although I don’t think that is an appropriate question either.”

“Hey, listen, I said I would delete your number if you wanted me to. Do you want me to?”

“No, you can keep it for emergencies, I suppose.” Castiel said and immediately started to blush. Dean’s stomach did a flip at the smile that was on his teacher’s face. His mind flashed to his car and the back seat and him looking down on Cas. He pulled himself out of his fantasy and responded quickly. 

“Anyway, 31 isn’t that old, plus he’s kinda cute.”

“Yeah he owns a bakery in the city. It’s called Trickster’s Treats, he makes the best of the best.”

“Maybe I’ll go try it sometime, a drive to the city doesn’t sound too bad.” Dean said with a light laugh and smiled naturally.

“Yeah, I’m going up this week, maybe I’ll bring back a sample for next Fri-“

“Hey can you help over here?” Jo yelled from the other end of the bar.

Dean’s head snapped in her direction. “Yeah. I’ll be right over.” He turned back to Castiel to see he was already gone.His heart hurt for a millisecond that Dean would not even admit to himself. He turned to Jo and helped her make the last round of drinks. At the very end of the night after the lights were off and the door was about to be locked Dean took three shots. One tequila, one fireball, and one Jameson. He sprayed the soda gun right in his mouth as a chaser. Jo scolded him but he just laughed his ass off all the way to the car.

When he arrived at the party he was starting to feel a little buzzed from his shots at the bar. He immediately found the kitchen and the beer. Over the loud music he couldn’t even hear himself think, though maybe his thoughts weren’t the best place for him to be right now. He grabbed a few cans of beer, poured one into a cup and took the other two out onto the patio to shotgun them. Tonight was his night to get drunk and he was not going to waste it.

He was constantly pushing past people who muttered half hearted complaints and he could not care less. After he was finished with two beers he pulled out his pack of cigarettes, which he swore he only smoked when he was drunk. The smoke rolled off his lips as he leaned against the side of the house and the door opened. All the other kids out there were smoking too so he did not look out of place. Benny just so happened to be the one that walked through the door. He did not see Dean at first and went to go talk to some other kids that were out there.

Dean did however notice Benny and watched the way his hips moved when he walked mesmerized by him, maybe that was the alcohol talking, maybe not. Either way he was well and truly fucked for the night. Once Benny laid eyes on Dean it was game over. They went inside together and ripped a few shots of whatever was left on the table, some vodka Dean thinks, something sweet, and something that tasted like cinnamon. After they maxed out on shots they went over to the, what seemed to be the living room, lord knows this house had too many rooms. Anyway the pong table was set up and Crowley was playing with Azazel, they were the kings of the table.

Benny called next to which Dean was slightly worried. He was good at pong but he also didn’t want Crowley to hate him anymore than he already does. They hopped on the table and started to play. It was fun and pretty intense if he was being honest. The first round they got balls back and Crowley sneered at Dean. A few rounds had passed and Dean went for the bounce and made it. The crowd that had surrounded them were half on Crowley’s side and half on Dean’s side, old captain versus the new. They all erupted with noise as Azazel took away two cups. It was finally down 2-3. Although Dean was in the lead, he knew he could not win, mostly because it was Crowley’s house. He purposely threw his next shot and the next round they won. Though the gloating was almost intolerable he let them take the win, Dean didn’t need to prove anything. Benny squeezed his hand knowingly and smiled warmly at Dean.

On the way up the stairs there was a lot of fumbling but nothing could compare to Benny’s hands running up and down his body. They made it into one of the guest bedrooms finally and locked the door behind them. The music was thudding beneath their feet. Dean was forcefully pushed against the wall of the room in the fancy house. He whimpered in the heated kiss as Benny flicked his perky nipples under the black shirt that he looked so good in. The two boys pulled away as they undressed each other to their underwear. "Do you want to move to the bed or would you prefer to be fucked against the wall?" Benny whispered sweetly in the brunette’s ear.

Dean shuddered with the sudden feeling of hot breath in his ear and buried his face in Benny’s chest. The larger blonde boy smiled and carried Dean bridal style to the large bed. Dean lay there on his back as Benny took in every inch of him. He immediately pinned his hands above his head and started to attack the vulnerable boy with kisses and hickies. Dean’s face was flushed and bit his lip, only to have muffled moans to escape. Benny smirked and traced his hands over the well-built body and hovered over a particular tent.

"Are you hard, baby?” He teasingly tapped the tip and watched as the pre-cum left a stain on the boxer-briefs. Dean’s breath hitched and he thrusted his hips upwards for more contact. Benny snickered at his partner’s attempts to gain any kind of friction. 

“Benny… Please!" He whimpered. 

The dominant boy twisted Dean’s nipples and received a gasp in return. "From now on, I want you to tell me when you’re about to come. Am I clear?”

His face was so close to the soaked tent, it almost felt painful for Dean, knowing that he could not force Benny to deep-throat his aching member. “Y-yes, now p-please suck my dick” Dean laughed nervously feeling exposed.

Benny smirked as he slowly pulled off both of their boxers, watching Dean glance at anything except for this boy’s eyes. Teasingly, the southern born boy spread apart Dean’s legs and sucked on the tall prize before him.

Dean arched his back and released a shaky moan of pleasure. "P-please suck f-faster Benny!” His voice was soon muffled by a hot kiss that left his lips red and puffy. The brunette looked down and watched as this man’s mouth sucked more and more of his cock, nearly choking every time he lowered his head. A burning sensation in his gut made him want to release his cum into the hot wet mouth.

It was starting to hurt to hold it in. “I-I, Benny, I’m so close…” Dean trailed off trying to last a little bit longer in his inebriated state. He felt Benny’s lips curl. His eyes widened as realization struck him. He was not going to stop. That was the last thought left before he saw pure white scenery as he came down Benny’s throat. The lips around his cock became tighter as he swallowed the load.

Benny pulled away with a smirk plastered on his smug face. “It’s been way too long baby, you didn’t last that long. Do you wanna come again?” The somewhat submissive brunette gave an incredulous nod as he struggled against the hands around his wrists. Being blown by Benny was always an adventure for him, especially when there was alcohol involved.

Whenever they would have sex, he would always switch something up. Letting Dean be on top and throwing around dildos and butt plugs. Given the setting few of those things were possible.

"AAhh~!" While lost in thought, Benny took his hands away as Dean felt two fingers moving around his ass, look for his prostate. They felt so slippery and easily spread his hole, the simulation was enough to make him hard again.

His loud moans and pants blended in with the music pounding just down stairs. He knew exactly where Dean enjoyed being touched and how to give him a bigger wave of pleasure. “M-mm! Y-you can fuck me now!” Dean’s face was completely red. His eyes were half-lidded with drool coming out if his strawberry lips.

Benny added another finger and thrust his fingers faster, deeper. The brunette arched his back. Soon enough, his member was fully hard and was leaking pre-cum on the ruffled bed.

Benny’s sultry voice became quiet while licking back up to Dean’s neck. The bottom boy’s legs were soon propped up on the other’s broad shoulders for easier access to the pretty pink asshole. Benny quickly slid a condom on before surprising Dean— be safe kids!

The line backer’s member was teasingly pushed against the clenching hole until he rammed himself in without any warning. Dean screamed for anyone listening close enough to hear that he was being fucked dry by his teammate. "I love the way your body reacts to my dick. When you arch your back and call out my name, I love it." Benny huffed and moaned as he repeatedly slammed himself over and over again into this juicy ass.

The pleasant feeling of a wet surrounding, tightening around his hard member was amazing. “C-Benny F-faster please! I-I want you t-to go fahh-!" Dean was unable to finish his sentence as Benny pulled Dean up on top of him. Gravity did its job and pushed the tight asshole against around this big cock. Benny let out a blissful laugh and paused as he bottomed out.

"I want you to ride me, Dean,” The look of mischief lingered in Benny’s hazel eyes as Dean swallowed his drool. 

“O-okay anything you want.” Dean pulled himself up with his knees and let himself drop back down and picked up the pace. He leaned into the other boy’s ear and whispered "I want your big fat juicy cock to slam into me until I see stars!"

Benny’s smirked returned as Dean repeatedly slammed his prostate and let out a string of obscenities. Benny pulled Dean down to kiss him with lots of tongue and biting. He moved to his collarbones and shoulders and left a few purple marks that Dean would have to cover up with make up so his teachers didn’t see. Why was he thinking about his teachers— scratch that, teacher— while riding his friend’s insanely good dick?

Benny’s mouth was still on Dean’s neck as he moaned and and said he was close. Dean pulled off and replaced himself with his mouth. Benny came soon after, letting out a lewd moan of Dean’s name.

The sight alone was enough for Dean to come into the sheets that were not his and not even care. A few seconds passed before either of them said anything. “That was amazing,” one of them sighed, blending together with all the sounds around them. They laid there with Dean’s head on Benny’s thigh and said nothing for a long time.

“We should probably get back downstairs.” Benny said matter of factly, not making any moves.

“Yeah,” Dean agreed, but to their surprise they just fell asleep. Dean was so tired, and apparently Benny was too.

**Notes for the Chapter:**

> what do you guys read on? also my next chapter will hopefully be up in two weeks


	5. Breakfast

**Summary for the Chapter:**

> Dean get's a moment to address some of his trauma.  
> Lisa is back and better than ever. I don't know what else to say, they have breakfast.  
> Everyone loves Lisa, who doesn't ;)  
> CLIFFFFF HANGERRR

There was a knocking at the door and a voice he recognized. The door swung open, but for some reason Benny was not by his side. His vision was blurred so he rubbed his eyes. Dean could finally make out the person in the doorway that was spilling light into the otherwise dark room. Castiel stood before him in a white button up, black slacks, dress shoes, a blue tie that brought out his eyes, and of course his trench coat. Soon Cas closed the door and relocked it behind him. Dean’s head cocked to the side, but was only met by a wicked smile on his teacher’s face.

“Are you ready Dean?” The older man asked dropping his trench coat onto the floor

“Ready for what?”

“Ready for this…” Castiel sat on the bed before Dean and leaned forward. Their lips met crashing into each other, hands reached out to caress the younger boy’s body.

Dean loved every second of it and started to loosen Cas’s tie. The teacher crawled on top of him and kissed down Dean’s already naked body. He reached Dean’s hardening member and took it in. Dean gasped and sat up in the dark room he was in with Benny by his side.

To his surprise his dick was hard, his dream had felt so real. Since yesterday Dean hadn’t been able to keep his mind off his teacher even though he knew it was wrong. He had never thought Castiel unattractive albeit a little dorky, but he had never thought of Cas in this way either. Whatever it was he had to get it under control as soon as possible.

Dean grabbed his phone to check the time and it read 5:15am. Benny was still asleep beside him. In order to avoid waking him up Dean snuck out of the room and put his clothes on, no one seemed to be awake yet until he reached the kitchen. Lisa was in there making coffee and cleaning up because she’s just that good of a person.

“Hey,” Dean said head pounding from all he drank last night.

“Oh! Hi,” she replied quickly, startled by his voice. “I didn’t think anyone else was awake yet.”

“Neither did I.” He chuckled nervously and scratched the back of his neck.

“Did you have a good time last night?” Lisa asked a bit awkwardly.

“Yeah, I did, I haven’t let loose in a little while and yesterday threw me for a ride.” Dean said honestly.

“Me too. It was good to see you at the diner. And here tonight.” She turned back to making coffee and cleaning up the endless bottles and cups laying all around them.

“Yeah, thank you for tipping, we really appreciate it. How have you been?”

“I’ve been good, I’m finally cheer captain, so not too bad” She looked up and smiled at him. He missed her and that look made him remember that she must feel the same way.

“Maybe we could hang out sometime? Grab a coffee?” Dean asked, moving over towards the cupboard full of mugs.

“Yeah, that doesn’t sound too bad. One day when neither of us has practice and you don’t have work…” She trailed off, smiling. None of those things ever happen all on the same day. Dean laughed at her smile and he felt happy. Lisa was not only his girlfriend most of sophomore year, but she was also someone who knew Dean and everything he went through, which was rare to come around these days.

He smiled again and apologized. “I’m sorry.”

“Sorry for what?”

“Everything I put you through?” Dean smiled sadly at her. Their break up had been rough on the both of them especially because neither of them had really wanted it. He regretted cheating every single day, but he couldn’t take it back. Dean could picture everything that happened that night and all the weeks that followed. He never wanted to lie to her so he didn’t. She said they could make it work but he wanted to find himself first, as cliche as it was. He ended up finding Benny in all of the chaos. Although his southern boy-toy was nice, he wasn’t Lisa.

“That coffee definitely sounds good, when are you free?” He asked after she had a minute to let his words sink in. It seemed that she snapped out of a little daze of her own when he asked.

She looked up at him and smiled softly. “I’m actually free today if you are?”

“Yeah, I just have to check in with Sam first.” He hitched his breath as though he had revealed something that he didn’t want to. As quickly as he inhaled he exhaled his breath, he had nothing to hide from Lisa.

“Oh yeah, how is the little guy?”

“Hah! He’s not so little anymore. He’s going to be taller than me soon, but don’t tell him that. He got really into soccer actually, he’s looking good to make captain next year, as a freshman.” Dean said with stars in his eyes, the way he always did when he talked about his baby brother. Sammy was his pride and joy.

“Wow I can’t believe he’s going to be a freshman next year.” She chuckled.

“Yeah, it’s crazy, I feel like we were kids just yesterday.” He said as he pulled out his phone. “Just give me a sec, he’ll love to hear I’m talking to you.”

It rang for a few seconds and his younger brother picked up the phone with a groggy voice. Dean laughed and said “Hi. Whose house are you at today?”

“My buddy Andy’s house.” A tired voice came through the other end of the phone.

“How much longer can you stay there, do you need me to pick you up?” Dean asked, looking at Lisa as she busied herself pouring them coffee. She had a certain elegance to her, the way she moved and talked.

“I have at least a few more hours here, why?” Sam asked on the other end a little bit concerned if he was being honest.

“I was going to go get some breakfast with Lisa.” As he said her name she looked up and blushed a little bit.

“Oh it’s breakfast now? Here I was thinking it was just coffee.” She laughed at him and he smiled back. The kind of smile that made his eye’s crinkle. The smile that Lisa always managed to bring out of him.

“Oh, nice, you guys getting back together?” Sam asked on the other end of the phone. Dean was lost in the moment with Lisa as they stood there smiling at one another.

“No, I don’t think so, I think it’s better than that.” Dean said simply. “Call or text when you need me to pick you up, or if anything goes wrong I’ll be there.”

“Yeah, yeah I know the drill Dee, I’ll be in touch.” Sam said before he abruptly ended the phone call, without saying goodbye. Dean texted him anyway.

5:45 am  
Dean [Hey, I don’t even get a goodbye now? How about “Wow Dean you’re the best big brother ever, I love you!”]  
5:47 am  
Sam [Whatever, I’m tired, enjoy your “not-date-date.” I love you, BYE!!]

Dean could practically hear his brother's infamous sarcasm and his bitchface through the text. He laughed to himself and turned back to Lisa who was looking out the kitchen window at some birds on the bird feeder. There was a small smile on her lips, for a second he just admired her beauty. Finally the birds she was watching flew away and she looked back at Dean. His eyes were fixed on her, thoughts trailed off to somewhere unknown.

“Hey, is your brother okay?” She asked, sounding slightly worried.

“Oh, yeah he’s fine, you wanna head to breakfast, my diner is 24 hours.” Dean snapped out his thoughts about how gorgeous Lisa really was. He smiled and moved over to her, almost close enough to kiss. A hand was soon placed on her shoulder and he kissed the top of her head.

“Let’s go,” She blushed slightly and slapped him in the arm. She grabbed a sweater that was thrown over the back of one of the chairs at the island in the enormous kitchen they were standing in. He followed her out the door grabbing her hand as she led them to his car. Baby, who she knew a little too well was the same as she would have remembered, including the same cassette tapes.

“I’m happy we’re doing this.” He said as he grabbed her hand. She laced her fingers through his and slid a little closer on the bench seat. Dean had definitely missed this more than he thought he could.

They took the 20 minute drive into town away from “rich people territory” as Dean liked to call it. The McMansion that the MacLeod’s owned was on the outskirts of the suburbs, Dean lived closer to the inner town in a much smaller neighborhood, and the diner was in downtown Lawrence.

On the way there, their conversation was light and easy. It was all reminiscing and happy memories. Lisa picked out her favorite cassette that Dean had and played “Nothing Else Mattered.” Dean argued with her saying that the song was overplayed just because it was popular, they had much better songs. She argued back saying that there was also so much more to music than Metallica and Led Zeppelin. They laughed and Dean was good, they hadn’t spoken many words since the official end of their relationship. Thank goodness Lisa was not the type of person to go around spreading rumors of cheating and Dean’s secrets.

They pulled up and Dean put the car in park but neither of them made a move to get out of the car. She took her hand out of his and placed it on his face. She rubbed her thumb across the stubble that was a few days old. He closed his eyes and took deep breaths and finally placed his hand over hers. He brought her palm to his lips and kissed it gently. The look in her eyes when he finally opened his eyes let him know that she was okay, she had forgiven him.

Finally he leaned forward and kissed her. The spark that they shared was still there. The kiss was sweet and passionate at the same time. Old lovers coming back together, like the stars aligning after years out of focus. Dean pulled back first and Lisa didn’t fight it. A tear rolled down her cheek and Dean was quick to wipe it all away.

“I’m sorry” she sniffled.

“It’s okay” Dean said, pulling her closer and kissing the pretty dark brown hair on top of her head. He inhaled and got a whiff of her conditioner, it smelled the same as he remembered and chuckled to himself.

Lisa pawed at his chest pulling him away as his laugh continued to grow louder. “Don’t laugh at me!” She said defensively rubbing away any sadness that was on her face replaced by an endearing look of bewilderment. He was laughing at her.

“I’m…sorry…it's…just that…you use the same… conditioner,” Dean explained through laughs that he still couldn’t contain.

“You ass, it’s my favorite, cherry blossom.” She countered his laughing, but gave in soon enough. They sat there laughing for a little while.

Once they calmed down Dean rubbed away a tear before it fell from his eye. He took her hand again and she looked at him ever so innocent. “You are amazing.” He sighed at her, tucking her hair behind her ear. “You are beautiful, no, you’re gorgeous.” He said running his thumb across her rosy cheeks. “You deserve the best, better than me, better than anyone in this town.” She looked up at him with wide eyes.

“Dean…” He cut her off with his finger trailing over his lips.

“Lisa…it’s okay.”

“No, Dean, I want this.”

“No, Lisa, you don’t want this, I’m a mess, plus there’s Benny now, and I just, I need to make it to January and then I should have enough saved up for an apartment.” Dean let out a big breath.

She leaned forward again kissing him lightly. “Friends then?” She asked sadly, knowing he was not going to budge on this issue.

“Friends sounds good” He said against her lips and smiled before kissing her again. “I just, I don’t want to rush anything. My biggest regret is hurting you, especially the way that I did Lis.” Dean pulled away from her so she could see the sincerity in his eyes.

“I know, Dean. I know.” She said returning the stare while he teared up a little bit. He pulled away and wiped his eyes before any tears could fall.

“Ugh, I’m starving.” He said scratching the back of his neck. The car door swung open and it surprised Lisa, she jumped and laughed at herself. Dean walked around quickly to get the door for her.

“Ah, so chivalry isn’t dead?” She queried jokingly

“Not as long as I’m alive.” He held out his hand to help her out of the car, keeping the joke going a little longer. She stepped out of the car and linked her arm through his elbow and smiled at him.

When they got inside he saw Dorothy right away. He moved with Lisa a step behind him to her section. They plopped down inside a booth on either side. Dean thought it was very strange when two people sat on the same side of the booth. However, under the table their feet kind of tangled together and they started another random conversation about school.

“What’s your favorite subject?” She asked lightly, tracing her hand over his knuckles and holding the menu with her other.

“Uh, Art I think, it’s an easy stress reliever, then probably History.” Dean answered smoothly. “What’s your least favorite?” He countered.

“Uh, I think science is my least favorite. How about you?”

“My least favorite class definitely has to be Math. Dr. Finnerman, it’s so weird that he forces us to call him Doctor. I’ve definitely seen him checking out some of the girls in my class.”

“OMG! Mine too!! He’s a freak and I think I’ve seen him look at my ass, which is weird for how strict he is.” She laughed cringing.

Dorothy walked over to the table as their laughter died down. “Hey Dean!” She beamed and smiled at Lisa as well. “Oh! You were here the other night, the nice girl who tipped!” Dorothy smiled even bigger somehow.

“You must be tired,” Dean chuckled sympathetically.

“Oh you bet I am! Three more hours, amirite?” She laughed back, smile dimming a little bit. “What can I get you guys?”

“I’ll have the Waffle with extra strawberries please” He batted his eyelashes at her jokingly. She smiled and wrote down his order on the pad in her hand.

“And for you?” She said turning towards Lisa again.

“I’ll have a Western Omelette with spinach and broccoli instead of onions please. If you can do that, if not that’s okay.” Lisa was oddly nervous. Dean thought it was very cute but knew he still couldn’t do anything about it.

“Yeah we absolutely can! Do you guys want anything to drink?”

“I’ll take iced water, an orange juice and a chocolate shake please?! Oh yeah! Can I have two sides of bacon with my waffle please?” Dean gasped because he couldn’t believe he had forgotten his bacon.

“Yes two sides of bacon, gotta have that protein.” Dorothy responded rather sarcastically.

“I’ll just take a water, no lemon.” Lisa piped up before Dorothy could walk away.

“Absolutely, I’ll go put in your order and I’ll be back with drinks.” She said cheerfully before walking away.

“Who’s that?” Lisa asked after Dorothy was out of earshot.

“Oh, my co-worker, we got to talking yesterday, it’s actually pretty nice to have a friend that’s out of high school. She understands the stupidity of cliques and drama. No one really should care who’s dating who, ya know?” He said in a quick breath, something he had been wanting to get off his chest to someone for a little while now.

“That’s good that you’re making new friends, I’m proud of you.” Lisa said and Dean found a strange sense of comfort in the word proud, that was most definitely tracing back to his issues with John. However it was good for him and he was proud of himself. As much as he was the popular kid he was also the kid that took hits for his baby brother.

They sat there in silence for a little while, both of them lost in thought. Dorothy came back with their drinks, interrupting them. She smiled at them and said something about their food that Dean didn’t really hear, too focused on his thoughts. He happened to be thinking about school and homework and what he had to get done before tomorrow. Lisa was looking out the window of their booth at the cars passing on the road, she was clearly lost in thought as well. Once Dean came to he looked at her for a few seconds. Her eyebrow was furrowed how it always was when she was thinking.

“Whatcha thinkin’ about?” Dean chuckled as she realized he was staring.

“Nothing in particular,” she smiled at him.

Before he could ask another question their food came over. They both thanked Dorothy and went right to eating. The waffle was so good that Dean all but moaned when he bit into it. Balanced perfectly with whipped cream and strawberries, no syrup needed. He moved to the bacon after to balance the sweet with the salty. Lisa looked at him and laughed.

“What?” Dean asked with bacon in his mouth and whipped cream on his cheek.

“You have a little something” Lisa laughed even harder as he tried to lick the wrong cheek. He started laughing too.

She reached across the table and heard his phone ring on the table. He stopped laughing immediately and wiped off his hands to pick it up. The screen read clear as day “JOHN WINCHESTER” and the picture Dean had taken a few years ago when he was passed out drunk made Dean's heart drop.

**Notes for the Chapter:**

> I finished my finals so the next chapter should be out like next week or something like that.


	6. Tattoos

**Summary for the Chapter:**

> The boys get home  
> John Leaves.  
> We meet Bobby here :)  
> Cute brotherly bonding  
> Trigger warning (scars/mention of physical abuse)  
> There is a self love scene at the end, its long, but I worked really hard on it (female writing a gay man's pleasure of himself)  
> Yeah, Enjoyyyy

**Notes for the Chapter:**

> OMGGGG I AM SO SORRY THAT THIS TOOK SO LONG TO GET OUT. MOLLY WAS DEPRESSED AS ALL GET OUT. THIS IS ABSOLUTELY NOT A DEAD FIC AND I AM DEFINITELY WORKING ON NEW THINGS AND UPDATING AT A BETTER PACE. THIS CHAPTER IS A LITTLE LONGER TO HOPEFULLY MAKE UP FOR ME BEING GONE FOR SO LONG.

When Dean got home he was more worried about Lisa than anything else. He left her with the bill and no explanation . The sound of his fathers voice shook him on the phone, he came home so quickly he thought he was going to get pulled over. The front door slammed open and Dean looked up from his thoughts to an angry looking John. Yet he still could not figure out why his father was calling him at nearly seven in the morning.

“What took you so damn long?” John was strangely calm. Dean flinched at this unfamiliar polite tone. That usually meant that things were not going to go well for him.

“Sorry, Sir. I was at the diner in town. I didn’t think you would need the car back so early.” Dean replied clearly and respectfully.

“Oh, I can see where you might have thought that. Next time just be home as soon as you wake up. Where’s that little brother of yours?” John smiled at Dean.

“He has a sleepover, Sir. For a school project.”

“Are you going to pick him up?” His father asked, with another out of place smile. This was not the John that Dean had become oh so familiar with

“Of course, Sir, as soon as he texts me.”

“Go get him now, I need to speak with the both of you.” John lost control and snapped.

“Yes, Sir.” Dean stood up even straighter if that was possible. “Should I take the car or my bike, Sir?”

“Take the car and hurry up.” John gained his composure again. When Dean pulled away he saw John pull out a cigarette.

In the car Dean pulled out his phone to call Sam. He did not pick up at first, but after the third try he finally answered. “Hey!” Sam answered cheerfully. “What’s up?” Dean could hear him chewing on something, probably a pancake, those were his little brother’s favorites.

“Finish your breakfast soon, I’ll be there in five.” Dean paused for a moment. “Dad wants us home.”

Sam nearly choked on the other end of the phone. The ‘oh’ on the other end of the line was barely audible and Dean hung up. He watched the road in front of him getting blurry as tears threatened to fall. He blinked a few times and breathed very slowly. They ended up going away but the cause of them was still there. No son should react the way that Sam or he did when talking about their own father. John had failed them over and over and Dean was so sick and tired of it, but he always held it together for his Sammy. He was a mother and a father for that kid and he was damn proud of the brother he raised. Dean pulled up and Sam was out the door before he could even honk.

The younger boy got in without a word and they stayed like that as Dean drove for a little while. Dean did not know how long, but he was enjoying the quiet, it allowed him to think. Eventually Sam saw how white his older brother’s knuckles were from gripping the steering wheel so tightly.

“It’s bad, huh?” He asked quietly so he didn’t startle his brother. Dean nodded his head solemnly with a glance. He then loosened his grip, looked back at the road and the car was silent the rest of the ride.

**. . .**

Both of the boys rushed inside, expecting their father, but he was nowhere to be seen, or heard. “Dad?” Dean called out cautiously.

The house not only looked empty but sounded empty as well. Aside from the stilled breathing of Dean and his brother. They walked through the house on edge. The brothers simultaneously heard the back door open and close, they made their way into the kitchen and waited patiently for John to make his way to them. When he saw them there was an awkward smile planted on his lips.

“Hey, what’s up dad?” Sam asked nervously. Their father did not smile at them very often.

“I just wanted to let b both of you guys know that I am going on a hunting trip for 5-7 days. My friend Daniel - Daniel Elkins- is going to be here soon. I will keep in touch, but he should be here soon. I just thought it would be nice to let you boys know.” John smiled for the second time and his sons smiled back awkwardly. It was equally the strangest thing and the nicest thing John had done for his sons in years. “Oh, and I’m sorry for losing my temper this mor—“ He was cut off by a horn honking. “That's for me!” He patted Dean on the back before exiting with a duffel bag over his shoulder.

Sam and Dean stood there dumbfounded by what had just happened. Neither of them could comprehend if it was real or fake. Suddenly Sam started to laugh. Dean turned his head as Sam laughed even harder.

“Are you okay??” The older brother asked, genuinely concerned.

“I…Think…that’s…the…first time…dad has ever… apologized to us.” Sam said through laughs, in an attempt to calm down. Dean mulled over the words for a few seconds before bursting out into laughter himself.

“I think you’re right” he laughed along with his brother. Sam joined back in and they just laughed at the whole demeanor of their father. This was a first for them, they hadn’t laughed like this in a long time, especially Dean.

The brothers spent the rest of the morning laughing and looking back on the strange habits of their father. The very concept of him being kind to his sons seemed confusing to them. In the meantime Dean whipped up some eggs and toaster waffles for them to eat. He called Lisa to apologize and explain, to which they had another little chuckle.

After finally cleaning. Up it was around 10:30. Dean had work at the auto-shop in the next town over at noon, but helped to be early. Since John left them the eye to the car he asked Sam if he had any plans today.

“All right, you SURE you’re not going anywhere?”

“Yes Dee, I think I might have Jessica come over.” Sam slipped in her name quietly, hoping Dean would not notice. He did, but he let it slide.

“Okay, have fun.” Dean said “Wait up for me, there are new episodes of Dr. Sexy out.”

Dean was off to work at “Singer’s Auto Repair” where he worked weeknights after practice, but Sunday’s were usually free for him so he picked up an extra shift here and there. He turned on some low music and hummed along mindlessly. He was early to work at 11:30 as per usual. 30 minutes was no big deal, Bobby had come to expect this of the teenager. Bobby knew Dean all his life, just like Ellen. Only, Bobby knew John when Mary was alive and well.

“Hey kid, how ya been?” Bobby asked as Dean walked into the office.

“Good, how about you?” Dean had always liked Bobby, probably more than his own father at this point. He once took Sam in when Dean was sent to a foster home. John had just left them for one of his hunting trips when they were just 7 and 3 years old. John came back eventually and that’s when things got really bad for Dean, especially as he started to question his sexuality.

“I’ve been pretty good lately, even got myself a second date this week. Speaking of which can you close Wednesday night?” Bobby looked like he was blushing at just the thought of seeing this woman again.

“Of course, no problem!” Dean exclaimed, happy for his friend.

“How’s John?” Bobby asked knowingly, averting his eyes.

“Actually he just went on a hunting trip with his friend, uhh, Daniel… Elkins I think” Dean smiled brightly at this information.

“Oh yeah, I bet you’re awful happy about that huh?” Bobby chucked at the grin on the young man’s face. He scratched the back of his neck lightly before asking the harder question. “Has he been… rough with you boys lately?” He coughed awkwardly.

“Dean’s smile faded quickly before he responded.” Actually, no. He’s been pretty good lately. Sam and I are out of the house most of the time to avoid that sort of this happening. The scars are fading too. I have Sam put the medicine on them all the time. I think I’m old enough now that he will just punch and kick me, anything more is too much effort.” Dean vented, looking at anything but Bobby as he spoke. “At least he doesn’t smoke in the house anymore though.” Dean tried his best to play it off, holding his upper arm.

“At least he doesn’t smoke in the house anymore” Bobby repeated bitterly. Dean couldn’t tell if he was mad at him or his father… or both. Either way he didn’t want Bobby mad.

“Bob, ’s okay, I’m almost 18, we will be out of there before you know it. If I don’t take it now it will go toSam and I can’t even bore that thought.” Dean comforted this boss in any way that he could. He sighed before clocking himself in, it did not seem like Bobby would be saying anything, anytime soon.

**. . .**

  
Dean’s day was going fine and his shift was almost over. He had to get to the roadhouse by 8 to cover part of Jo’s shift. He kept checking the clock, because he forgot his watch back at the house. No way was he going back there with Sam and his GIRLFRIEND.

He was under a car doing an oil change when he heard a familiar voice. He nearly hit his head while getting out of his position. Since it was getting more into the fall the heat was usually on in the garage. The heat mant Dean was in a take-up and covered in grease. He brushed his hands on his jeans before walking towards this voice.

Bobby was making small talk when Dean walked in.

“Hey!” He said awkwardly, bringing the attention to himself. The two men looked over and just stared, waiting for him to say something else. Dean just stood there nervously, fiddling with the hem of his tank top.

Castiel looked just as casual as the last two days Dean had seen him. A plain t-shirt, this one was dark maroon, jeans and his trench coat. But today as Dean stood there he noticed part of a tattoo peeking out from over his shoulder. It looked like the tip of a wing. For a split second Dean wanted to ask him to expose himself as he had made Dean do, make him feel vulnerable.

“What’s up Dean?” Bobby finally said after what seemed like an eternity.

“This is my teacher, I told him to come here because of your good prices.” Dean all but blurted out.

“So I heard from my new friend here” The old Bearded man gestured.

“I’m not sure we’re friends yet.” Castiel retorted awkwardly and a bit confused.

“It's just an expression, all my customers are friends.” Bobby explained looking back at him.

“So, what’s wrong with your car?" Both eyes turned back to Dean.

“I think it's the muffler, but I could be wrong.” Castiel responded.

“Let's have a look," Dean threw on his sweatshirt to go outside.

Bobby stayed at the desk while Castiel led Dean to his car. When Dean laid eyes on the same gold pimp-mobile " he saw at The Roadhouse he started to laugh. “This… this is your car? Of course this is your car.”

“What ? What's wrong with my car? I like it"

"This is a-a-a _pimpmobile_ ” Dean laughed more. "No wonder something is wrong with the muffler, this car is ancient."

"Hey ! Look Who's talking Mister Leather-Jacket-and-1967-Chevy-Impala. You have no room to judge.” Castiel huffed back.

Though his words clearly had little thought behind them, they hung in the air for a bit too long. Dean realized that his teacher had to pay attention to details. More importantly, Cas pays attention to him.

"Hey at least I don't have any secret tattoos" Dean referenced what he saw earlier after a minute, he mostly wanted to get a rise out of the older man, he was also curious.

“Oh, you saw those?” Cas chuckled nervously rubbing where they would have been visible

“Yeah maybe next week you take your shirt off.” the green.eyed boy joked.

“Dean that would be highly inappropriate.” Castiel responded, but his voice dropped at least an octave, signaling to Dean he had considered what that would be like.

“I’m just messing around Cas , don't worry" Dean said to calm his teacher down . Although he did find the tattoos a little mysterious.

"It's Cas now is it Mister Winchester?” Castiel punctuated his student’s last name. The nickname did sound good though , not many of his colleagues found it easy to pronounce his name. Maybe Meg’s name would catch on. As long as it was not ‘Cassie’ as Gabriel insisted on calling him.

“Cas is fine, as long as it is after school, I come to your job, not once, but twice. You have earned it.” He said somewhat sternly with a small smile.

Dean laughed and gave a bright smile, something he seemed to be doing more genuinely since Friday afternoon. The thing was that Dean finally felt seen by someone other than his friends . An adult trusted him and was looking after him. Someone who didn't even know John . Someone Dean felt like he could trust too.

Alrighty Cas let’s take a look at your muffler." Dean said before crouching down at the back of the car. "This thing is rusted from the inside out. The rain this summer probably didn't help." The younger boy gave his judgement of the car. "You don't know much about cars then?"

“No, my father wasn't around, my older brothers raised me.” He stated matter of factly.

“Oh nice, that's what I do for Sammy. The only I know about cars is because it was the one thing all three of us could agree on when Sam got old enough.” Dean responded honestly. “Anyway, I would set up an appointment with Bobby inside for sometime this week. If you are dead set on me working on your car I'll be here Tuesday, Wednesday, Thursday from after practice until close, at nine. It should take an hour or two to replace the unit. It'll be about $500, is that okay with you?” Dean thought over any other information that he could have missed, but could not find any. He headed back inside to set an appointment for his teacher’s muffler.

His phone buzzed in his pocket to a text from Jo.

8:15 p.m.  
Jo [Hey! I don’t need you to cover me tonight after all, it’s not that busy.]

Dean sighed in relief and walked back into the garage to finish up his work on the last car of the night. The belt was basically torn to shreds. After an hour or so the clock finally hit 9pm and he cleaned up his station, wiped any and all grease he could see off his body.

“Hey Bob, I'm headed out of here okay?"

“Sure thing kid, I'll finish up this last paperwork" Bobby sighed, he had been doing this job too long. “Call me when you get home, yeah?”

“Mhmm” Dean muttered as he clocked out.

Sam was waiting for him at home. Dean saw a strange car out front with a man sitting in it. He knocked on the window to ask who he was. The man rolled down the window cautiously.

“Hey, who are you?" Dean asked kindly.

“I’m, uh, Jessica's father" The man sounded unsure of himself.

"Oh! Well I'm Dean, Sam's older brother.” He replied excitedly. "It's Mr. Moore right?"

"Yeah, I'm just waiting on Jess,” he said more calmly.

“Oh, I'll send her right out." Dean said with a laugh.

He proceeded to walk up to the door and unlock it. “HONEY, I'm home!" He all but shouted. There were muffled voices in the living room. Then the two kids appeared looking rather disheveled. Dean chuckled, he could see a dark hickey on Sam’s neck. There was another very clear hickey on Jessica’s neckline.

"Give her your sweatshirt”

“why?" Sam asked, confused.

“Look,” Dean gestured to his girlfriend's shirt.

"Oh, damn.” Sam said, stripping his sweatshirt for her. She happily accepted and put the hood to the right side.

“Bye Jessica, your dad is just outside.“ Dean smiled. He walked away so they could say goodbye. He promptly eves dropped, though all he heard was an awkward goodbye, a ‘see you at school,’ and a kiss. The door closed and Dean snickered around the corner.

"Shut up.” Sam sighed. “Why didn't you text?”

“To be honest, I completely forgot she was here. I was headed home to see you, when I saw her dad's car in the driveway." Dean said, his mischievous grin fading to a brotherly smile.

“Ugh! Fine, well you wanna watch a movie? I think there's something on," Sam replied, moving on from the embarrassment

"Actually can we watch Dr. Sexy?" Dean said somewhat nervously, instinctually looking over his shoulder for John.

“Careful Dean, your gay is showing.” Sam laughed at his guilty pleasure

“Whatever, nerd. At at least I don't have a hickey on my neck the size of Jupiter." Dean huffed back immaturely.

“Mhmm, take off your shirt and let me see that chest, huh?” Dean’s face flushed. “That’s what I thought, Jerk.”

“Bitch.” Dean rolled his eyes before turning the channel to his favorite show. Even though Sam would never admit to it, he liked the show too. He also enjoyed the time spent with his brother.

After four or five episodes, Dean made Sam go to bed because they had school tomorrow. Sam seemed annoyed, but he didn't argue. Dean stayed downstairs to straighten up the living room and the kitchen. He smiled at his work, then headed upstairs.

Once he plopped down on his bed he knew he was beat. He peeled his jeans off of his body, followed by his shirt. He climbed under his comforter in his boxer briefs. Tonight was the end of his always long weekends. He slid his hand under the band of his underwear and sighed heavily at the release of tension.

His mind ran to the previous night, the way Benny was so assertive over him. With his free hand, he ran his fingers over the lips that were kissed heatedly. They trailed over his neck and caressed each of the red marks that were left embedded into his skin. Dean’s unoccupied hand slid up and down his hardening member. As the fantasy progressed he tweaked his nipples, just like Benny had done, remembering all the dirty talk the southern boy was whispering.

Dean grabbed his lube and a vibrating dildo out of his bedside drawer. He left his dick unattended to drip pre-cum on his stomach, getting tangled in his happy trail. Dean liked to keep himself clean, he even routinely had his ass waxed. He was always one for manscaping too. Since his first time disaster story in which his partner ended up spitting out his curly hair, he learned his lesson.

The lube dripped onto his fingers, it was cool and he knew it would feel better than the rough condom from last night. He cringed internally as he remembered some of the things he said in the heat of the moment. Dean turned on his side so he had easy access to himself. His lubed fingers found their way to his tight opening, while his other hand fell back to his hard cock.

Starting with a slow pace was something Dean always liked to do to tease himself, he knew what he liked. The slick, lubed fingers were brushing his hole, before sliding two in with a small hum of pleasure. Dean fell back into his fantasy, but when he closed his eyes it was no longer Benny bending him over. He found himself imagining his teacher bending him over his desk. Although Dean was surprised, he ran with it — as long as it makes his dick hard right?

Two fingers inside him quickly turned into three when he felt himself growing harder. He tried to keep himself at a steady pace, but after he hooked his fingers to hit his prostate he bucked his hips up, unconsciously moving his hand faster. After a few seconds his breathing and his hand slowed. He gently removed his fingers from his ass only to shove the dildo in his mouth so it was slick, his mind slipped into thoughts of what it would feel like to have his teacher’s dick in his mouth. That simple thought turned Dean on way more than it should have. His cheeks hollowed as he pulled it out to fill his hole again, but the vibrator was much more satisfying than his fingers would ever be.

The process was slow, but worth it, Benny really tore into him last night and he did not want a repeat of that. He let out a deep breath, being as quiet as possible when he bottomed out. The button for it to turn on was on the bottom, the setting was a low vibrating so it sent waves of pleasure through him without even moving. He had to stop himself from letting out a moan loud enough to Sam up, what came out was a muffled moan and his hips jerked up into his hand.

After finding a comfortable pace — pumping his cock — he started to move the dildo in and out. The silicone was curved to hit his prostate every time, so he knew he was not going to last much longer. He started to pick up the pace as he felt the heat rising in his stomach. Soon enough he could not handle anymore, he came, the name ‘ _Cas_ ’ spilling over his lips. There was cum on his hand and up his abdomen, the blankets were a mess, splayed out all over the bed.

He had a towel from his shower this morning laying beside his bed. The same towel that he was now going to use to clean up the mixture of cum and sweat from his body. He quickly remembered that the toy was still inside him, though it was no longer on. As he pulled it out his body jerked from the overstimulation of his prostate. He threw it in the towel along with the lube and dumped it on the floor to deal with in the morning. Though this was the first night Dean fantasized about Mr. Novak, it certainly would not be the last

**Notes for the Chapter:**

> Thank you guys for sticking with this, let me know how you feel about the story as it progresses? ALSO WHY DID I NOT KNOW UNTIL TODAY HOW TO CHANGE THE TEXT SO YOU CAN ITALICIZE THINGS???? catch me italicizing like crazy in the future lmaoooo


	7. A Day in the Life

**Summary for the Chapter:**

> I did work to make this make sense, but here is a layout of his schedule and his teachers:
> 
> Period 1: Spanish 3 - Señorita Carmelita - 7:25 - 8:10  
> Period 2: AP English Literature - Mr. Ketch - 8:15 - 9:00  
> Period 3: Pre-Calculus - Dr. Finnerman (Raphael's vessel's last name) - 9:05 - 9:50  
> Period 4: AP European History - Mr. Novak - 9:55 - 10:40  
> Period 5: International Foods - Ms. Klein - 10:45 - 11:30  
> Period 6: Lunch - 11:35 - 12:20  
> Period 7: Human Anatomy - Mrs. MacLeod - 12:25 - 1:10  
> Period 8: Intro to Drawing - Ms. Masters - 1:15 - 2:00
> 
> This is specific to Dean, obviously.

**Notes for the Chapter:**

> I do not preview these chapters, sorry for any mistakes

All Dean could think about the next morning was his teacher, and not in a school related context. He even had to take care of himself in the shower. Dean felt dirty in both meanings of the word. Everything that happened over the weekend with ‘Cas’ — god Dean loved that nickname — made him see all of his teachers as people rather than mindless drones.

First thing he did when he got to school was meet up with Charlie. For him it was the hardest to figure if he wanted to tell her about the interactions from work, on not one but three occasions.

“Hey dude, I didn’t hear from you all weekend. What gives?” Charlie said with a hurt tone of voice as she bumped into his side.

“Hey! Sorry about that, you know how my weekends are.” He excused his actions.

“Whatever, why didn’t you invite me to that party on Saturday?” She complained again.

“Pfft, you think I don’t know that your Dungeons and Dragons group meets every Saturday? Don’t even try me with that Charlie. Plus you hate parties, no one is weird enough for you.” Dean smiled, satisfied with himself.

“Ya, okay, fine, but tell me how it was anyway.”

He put his arm around her and smiled. “Well, Friday work wasn’t too bad. Saturday was long… too long for my liking. I introduced myself to this nice girl at work, I think you’d like her actually. The par-“

“C’mon, just because I’m gay doesn’t mean that every girl is attractive to me.” Charlie interjected.

“Well, A. I didn’t say that you should date her, just that you would like her ‘vibes.’ B. Let me finish, you’ll have your turn.” Dean huffed at her. “Anyway, the party was good, I almost beat Crowley in beer-pong, but I didn’t want to humiliate him in his own home. Uhh, then Benny and I had some great drunk sex-” 

Charlie shivered out from under his arm at the mention of two men — Benny nonetheless— having intercourse. 

“Ugh we were safe and fell asleep together.” Dean lovingly punched his friend’s arm. “Hmm, what else… Oh YEAH! Lisa and I had a moment of closure and forgiveness which was really nice. Then we almost had breakfast at The Diner, but my dad called me and now he’s gone for the week or something. Worked the auto shop Sunday, then home, and that’s about it.” Dean finished. “OH! I walked in on Sammy and his girlfriend! It was freakin’ hilarious.” Dean practically shouted before Charlie could ‘sush’ him.

“Wow, I guess your weekend was long.” 

_Yeah, but I didn’t even get to tell you the best parts_. Dean thought to himself.

“Yeah! Now tell me all about yours before class starts.” They were leaned up against the lockers outside Dean’s Spanish classroom. Charlie’s French class was one floor down.

“Okay, well Friday after you left Gilda came over to watch a movie and talk about D n’ D. Then, as she was leaving we TOTALLY kissed on the front porch.” Charlie said excitedly. “All day Saturday I had to work at the Video Store, someone called out sick so I had to double. Uh, then obvi I had D n’ D at night. It was super duper fun and I got to see Gilda again. Except she was a fairy and I was a warrior, but we ended up working together. Sunday a nurse came for a check-up with my mom. I made breakfast in bed for the two of us. Nothing really special happened after that, I worked at The Store again and went home.” Charlie finished her recap out of breath from talking so quickly.

“Ahh, you and Gilda are so cute! I’m happy for you, Charles. Who kissed who first? I know you have been crushing for a few weeks.”

“She kissed me! That's the best part. I wasn’t sure if we were just hanging out because of Dungeons and Dragons, but I guess not!” Charlie squealed. “I’m happy for you too. You and Benny seem really good. Any Lisa drama?”

“No, actually good on all fronts. I just don’t want to get really involved with anyone right now, so I made that clear to both of them.” Dean smiled, impressed with his own maturity.

“Wow Deeean! Color me i-“ the bell cut her off “impressed.” she finished. They hugged before splitting up.

When Dean walked into his Spanish class his jaw dropped. Instead of Señor Roman there was a rather attractive blonde woman at the front desk. Dean found his usual seat towards the back. The class collectively stared blankly until the final bell rang.

“Hi folks, I am Señorita Carmelita.” The busty blonde’s voice echoed in the quiet classroom.

“Hola Señorita.” The class eventually answered.

“Your teacher, Señor Roman is on leave for the rest of the semester so I will be taking over for him.” She smiled widely at the class. She somehow managed to sound mature and young at the same time.

After her announcement Dean checked out of class, he was already fluent in Spanish, he was only in this class because a language was required for three years to graduate. Going between thinking about his AP European History teacher and his new Spanish teacher proved overwhelming. He took the necessary notes and finished the handout before class was over. Spanish was not looking too bad for the rest of the semester.

Dean’s next class was AP English Literature (AP Lit) with Mr. Ketch. He first met his teacher last year when he was just a substitute for his Honors English 2 class. English was definitely his forte, the accent was a bit much sometimes though. In this class he had to pay more attention because it was Advanced Placement which meant a lot more work for him. Work that he always did at The Garage on weeknights, it was mostly boring readings and essays about books that Dean did not read. He would have liked to read the books, but it was not plausible between football and raising his little brother.

After what felt like mere minutes the bell rang. Charlie was waiting for him outside their math classroom when he got there.

“Hey, didja miss me?”

“Oh yes, my heart could barely handle it.” Dean feigned lovesickness.

“Good baby, never forget it” Charlie snorted when she called him baby.

“We studied hard right? Honors pre-calc is about to be our bitch.” Dean held his hand up for their secret handshake.

“In the middle of the hallway?” Charlie asked, surprised and embarrassed.

“For good luck. C’mon Charles.” Dean pleaded. She gave in and they soon were spinning around like idiots in the hallway.

“We got this in the bag.” Charlie smiled leading Dean into the class with their laced hands. They put their bags down and pulled out their huge calculators that cost way too much money — god they were nerds.

After the bell rang Dr. Finnerman passed out the tests to pass back. He gave some basic directions and said “After you turn in your tests, please take the homework for tomorrow that is in a stack next to the basket.” Lucky for Dean he sat next to Kevin Tran, the smartest kid in school. He and Charlie studied extra hard Friday though, so he probably would not need help.

Page one and two flew by for Dean, but there was an open ended question that took him a few minutes to get past. The final quadratic equations were easy enough to do with the calculator. The test was very similar to the study guide and he had been over most of the materials last year in Algebra 2.

He doodled on the pages for about 10 minutes until an acceptable amount of kids had passed their tests in. He got up behind this kid named Karen Giles and followed her paper into the basket.

“Okay everyone, start to work on tomorrow's homework. If I see a phone I will write you up.” Dr. Finnerman stated loudly for the whole class to hear. There were some heavy signs, but they were pretty used to their anal teacher by now. Dean grabbed the work he had just put away. He got three or four questions done out of 10, when the bell rang. He would have to finish the rest before practice today if he wanted to stay on top of all his homework.

It was a blessing to have John gone for a week or two. They did not have to work to avoid him. Sam and Dean got into a routine when John took these trips — though he had not been on one in a while. School to practice, to home, to work. Sam’s school got out at 2:30 as opposed to Dean’s 2:00; however this worked out for the practice-slash-pick-up situation. Since today was Monday both of the boys had practice after school.

Dean walked into his History classroom but his teacher was not there. Charlie sat in the seat next to him and smiled. “How do you think you did? You didn’t even wait for me.” She asked her friend.

“Oh, I think I did fine, it was just like we did on Friday.” Dean responded absentmindedly, still thinking about his teacher and how he hoped Cas would be there.

“Good thing you were sitting next to Kev, he’s stupid smart.” She laughed, implying cheating.

“Gasp, Charlie, I would never.” Dean laughed in a mocking posh accent. Although he did not cheat he knew Kevin would not mind. The amount of times Dean saved him from the football team was through the roof.

Just as Charlie was going to respond Mr. Novak walked in with a purpose to his steps. Dean started to sweat almost immediately. Today he looked different. Usually he wore his white button up with a blue tie — he must have had a million different blue ties— a black suit jacket with matching slacks and shoes. On top of all that he wore his iconic trench coat. Today he was wearing the pants, the shirt, the tie, but the jacket and coat were over his arm. Mr. Novak draped them on his desk chair and rolled up his sleeves.

“Hey guys, sorry I’m late, I was trying to get the heat turned down in my room. I guess it does not vary by room.” The teacher frowned, walking around to lean on his desk. “I know it’s hot, but let’s try to focus. I’ll open these windows to circulate the air in here. It’s only fifty degrees, it's NOT cold!” He forgot he was speaking to a class and lost his temper. “Sorry about that.”

Dean was none too focused on his speech about the heat, but rather paying close attention to the way he looked without his trench coat on. While he did happen to see him in much more revealing clothing this weekend, he had never seen him like this. The yell also caught the student’s attention. It excited Dean and made him fall into a daydream. He was staring at his teacher walking around the front of the classroom. 

Dean imagined himself walking up to the front of the class and pushing Cas down in his chair. With the rest of the class gone he would unbutton his shirt slowly, but leave it and the tie on him, just loose. The younger boy was on his knees working on getting his tight dress pants off.

“Dean?” Castiel’s voice rang in his head, but what started out as a moan in his fantasy became real. Charlie nudged him, hard.

“Here.” He smirked nonchalantly, like he was not just thinking about sucking his teacher’s dick. Cas smiled back, no teeth showing, unlike his smile this weekend when Dean saw him.

“I think you have some drool there Dean-o.” Charlie stifled a laugh. Dean wiped at his chin and sure enough he had been. His face turned red immediately, hopefully Cas had not noticed. Dean liked the sound of Gabriel’s nickname on Charlie’s lips though, it was friendly and fun.

The rest of the class was roughly the same: Dean zoning in and out, Charlie pushing him back to reality. In the beginning of class he worked himself up to a boner, so he readjusted and focused on making it go away. The brunette could not help but wonder why his teacher and why now? 

While Cas was objectively attractive, Dean had always focused on people his own age. Dean decided right there that he would have to get to know this guy before he put both of their positions on the line. His teacher proved to have a good heart and was very trustworthy from everything that he had discovered on Friday. Dean usually blamed his bruises on football, but somehow Castiel saw right through that, how did he see through that?

The bell rang after Cas had given them the chance to start the reading for tomorrow. Some obscure articles on the development of parliament in Europe Dean noted. He had taken AP World History as a sophomore so he had a little depth to his knowledge of Europe’s history. Thank goodness they did most of their work in class, he liked teachers that did not assign much homework.

On the way to Cooking class Dean was staring at a number on his phone screen. His history teacher's number to be specific. Ghosting his finger over the number debating between texting him or not. Charlie noticed this conflict within him, but did not say anything outright about it. She did not recognize the name or the number he was so worried over.

Dean liked cooking classes because it meant that he got to learn new recipes to test out on Sammy. Because they made stir fry last class, today they would be making something sweet to balance it out. By the end of class Dean was still thinking about the number in his phone, but now he had warm cookies in his hands.

Lunch went back and forth on Dean’s radar. On days that he could bring food he was happy to hang with his friends, but days that he could not made him wonder if anyone noticed. He could not get that stupid ‘free-reduced lunch’ because someone would have caught on to John. When he did not bring food he scarcely had extra money to buy food — every cent that he made went away towards the first few months rent on a new apartment. Even if they did not notice, his teammates would give him bags of chips here and there, but they never knew the extent of Dean’s struggle. In their defense he did a very good job at hiding it.

Today he had a ham and mayonnaise sandwich and a bag of chips someone instinctually threw his way. He laughed with his teammates, even Crowley. Lunch seemed to be the one place where all prior dispositions fell away. Benny gave him a wink from the table a little ways down, he smiled and brushed it off. The football players always left the lunchroom a few minutes early to get to their next class, or to just goof off in the hallways.

After the long trudge up three, no, four, flights of stairs Dean was tired and in no mood to deal with any of the MacLeods. Dean sat in the back of the class, waiting for Benny. The southern boy was sitting down next to him just as the bell rang. The red head at the front of the classroom looked about as terrible as the students in front of her.

“Any volunteers for presentations today? If not I have a video on the inner workings and functionalities of the frontal love for you guys to watch.” Mrs. MacLeod’s voice rang through the classroom and she winced at her own volume. When no one proved willing to present she set up the projector and put her head on her desk for the rest of the period. There may have been a few people paying attention, but Dean was not one of them. He went back to his phone and opened a text.

[Hey!] - DELETED

[How are you?] - DELETED

[What’s up?] - DELETED

[I can’t stop thinking about you.] - DELETED

Dean 12:58 pm

[Hi, I don’t know if you remember me, but this is Dean]

His heart began to race after he sent it, immediately wishing he could delete it. He turned his attention away from his phone and towards Benny who was scribbling something in his notebook. After a hand was placed on Benny’s he stopped and looked at Dean. Dean pocketed his phone and took advantage of their shared table in the back of the room. Because Dean arrived early he got the best seats for them. It did not matter where they sat, just that they kept the same lab partners.

Dean leaned into Benny’s face, cupping his cheeks in a fervent kiss. They were being quiet in the dark room. Dean knew it was wrong to use Benny the way that he was, for a distraction. Not that Benny wasn’t boyfriend material, but Dean always pictured him setting down with a southern girl. In addition they were not very public with their fling, as much as Benny tried to make it obvious.

It was not until Benny let out a disgruntled noise that they stopped in fear of getting called out. Dean’s mood shifted quickly and the southern boy took notice. There was a response on his phone.

Gabriel 1:08pm

The bell rang before he could read it. He grabbed his bag and hurried to meet Charlie by the art room, not giving an explanation to Benny.

Charlie was waiting for him by the door to Ms. Masters’ classroom. She was holding something that Dean could not quite make out. She quickly jutted her hand out and gave him an answer to the unspoken question.

“Sorry they’re in a napkin, but I know you love powdered donuts. I had a post-test party in my English class, we all aced it!” She said excitedly. “Suck it, Great Gatsby!” Charlie giggled at herself.

“Thanks” Dean blushed, taking the sweet treats from her hand and immediately shoving one in his mouth.

“Of course!” She smiled wide at the powder lacing Dean’s lips. Her arm reached out to gesture towards their last class of the day.

During class today they were assigned an in-class project. Dean did not mind projects, but this one, a self-portrait was not his favorite. There was a twist though, one half had to be how you see yourself while the other had to consist of how your friends may see you.

By the end of class Dean had a pretty good sketch of what he was aiming for. He had not thought about his phone until Ms. Masters told them to pack up. He pulled his phone out to read the text.

Gabriel 1:08pm

[Hey, I could never forget a face as pretty as yours. What do you need?”

Dean’s fingers were fast to reply.

Dean 1:56pm

[I heard you make some good pastries, any pie over there?]

Gabriel 1:59pm

[Of course we have pie, what do you take me for? - Location Attached]

Dean smiled at the quick response.

Dean 2:00pm

[Maybe I’ll come try your treats sometime]

Dean hit send before thinking about it and gasped as the bell rang.

He had practice.

**Notes for the Chapter:**

> This is weird, but like as I'm writing I have to keep going back to past chapters because I'm just straight up lacking on what I wrote into the story already.


End file.
